2.4. Characterization Data of Product 3 Is Listed Below
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3,3′-biindolin-2-one (
3a) [
27], 93% yield;
1H NMR (400 MHz, CDCl
3) δ 8.88 (s, 1H), 8.12 (s, 1H), 7.28 (s, 2H), 7.25–7.22 (m, 2H), 7.16 (t,
J = 7.6 Hz, 1H), 7.07 (t,
J = 7.5 Hz, 1H), 7.00 (d,
J = 8.0 Hz, 1H), 6.94 (t,
J = 7.5 Hz, 1H), 6.87 (t,
J = 7.5 Hz, 2H), 6.78 (s, 1H), 5.17 (s, 1H), 1.32 (s, 18H);
13C NMR (101 MHz, CDCl
3) δ 180.9, 153.0, 140.2, 136.9, 135.4, 134.9, 130.0, 127.89, 125.9, 125.8, 124.9, 124.6, 122.5, 122.0, 120.9, 119.5, 117.0, 111.3, 110.1, 57.7, 34.5, 30.3; infrared (IR) (film): γ = 3648, 3353, 2956, 2925, 1710, 1618, 1580, 1491, 1436, 1261, 826, 782 cm
−1; HRMS (electron impact time of flight (EI-TOF)): calculated (calcd.) for C
30H
32N
2O
2 452.2464, found 452.2462.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-4′-methyl-3,3′-biindolin-2-one (3b), 91% yield; 1H NMR (400 MHz, CDCl3) δ 8.73 (s, 1H), 8.08 (s, 1H), 7.20 (t, J = 7.7 Hz, 1H), 7.11 (t, J = 7.0 Hz, 2H), 7.04 (s, 1H), 6.97 (t, J = 7.6 Hz, 2H), 6.87 (d, J = 7.7 Hz, 1H), 6.71 (d, J = 7.1 Hz, 1H), 6.49 (s, 1H), 5.19 (s, 1H), 1.94 (s, 3H), 1.32 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 153.0, 140.1, 138.0, 136.0, 127.9, 126.1, 124.8, 122.2, 122.1, 110.3, 109.1, 58.3, 34.5, 30.3, 20.4; IR (film): γ = 3637, 3342, 2956, 2925, 1706, 1618, 1322, 1021, 910, 747, 664 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O2 466.2620, found 466.2621.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5′-methyl-3,3′-biindolin-2-one (3c), 93% yield, 1H NMR (400 MHz, CDCl3) δ 8.86 (s, 1H), 7.95 (d, J = 1.7 Hz, 1H), 7.21 (s, 2H), 7.15–7.07 (m, 2H), 7.05 (d, J = 8.3 Hz, 1H), 6.88 (dd, J = 11.0, 4.1 Hz, 1H), 6.84–6.80 (m, 2H), 6.68 (s, 1H), 6.66 (d, J = 2.5 Hz, 1H), 5.09 (s, 1H), 2.14 (s, 3H), 1.24 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 181.1, 153.0, 140.2, 135.3, 135.2, 135.1, 130.0, 128.5, 127.8, 126.1, 125.8, 125.0, 124.7, 123.6, 122.4, 120.4, 116.4, 110.9, 110.0, 57.7, 34.4, 30.3, 21.5; IR (film): γ = 3637, 2956, 2925, 1706, 1618, 1471, 1157, 910, 747, 695 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O2 466.2623, found 466.2621.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-7′-methyl-3,3′-biindolin-2-one (3d), 90% yield, 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 8.03 (d, J = 1.3 Hz, 1H), 7.28 (s, 2H), 7.16 (ddd, J = 14.8, 13.7, 8.0 Hz, 3H), 6.96 (t, J = 7.3 Hz, 1H), 6.92–6.87 (m, 2H), 6.76 (s, 1H), 6.73 (d, J = 2.5 Hz, 1H), 5.16 (s, 1H), 2.22 (s, 3H), 1.32 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 181.1, 153.0, 140.1, 135.3, 135.2, 135.1, 130.0, 128.5, 127.8, 126.1, 125.8, 125.0, 124.7, 123.6, 122.4, 120.5, 116.4, 110.8, 110.0, 57.7, 34.4, 30.3, 21.5; IR (film): γ = 3537, 3241, 2956, 2925, 1706, 1618, 1471, 1236, 1157, 910, 747 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O2 466.2620, found 466.2621.
6′-Bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3,3′-biindolin-2-one (3e), 88% yield, 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.24 (s, 1H), 7.38 (s, 1H), 7.21 (s, 2H), 7.19 (dd, J = 7.4, 3.2 Hz, 2H), 7.02–6.96 (m, 2H), 6.89 (dd, J = 8.1, 5.1 Hz, 2H), 6.74 (d, J = 2.3 Hz, 1H), 5.18 (s, 1H), 1.31 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 153.1, 139.9, 137.7, 135.5, 134.6, 129.7, 128.0, 125.6, 125.0, 124.8, 124.7, 122.7, 122.6, 122.3, 117.2, 115.7, 114.1, 110.1, 57.5, 34.4, 30.2; IR (film): γ = 3537, 3441, 2956, 2925, 1706, 1618, 1471, 1322, 1157, 910, 750 cm−1; HRMS (EI-TOF): calcd. for C30H31BrN2O2 530.1569, found 530.1570.
7′-Chloro-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3,3′-biindolin-2-one (3f), 89% yield, 1H NMR (400 MHz, CDCl3) δ 9.04 (s, 1H), 8.32 (s, 1H), 7.26 (s, 2H), 7.19 (t, J = 8.1 Hz, 2H), 7.10 (d, J = 7.5 Hz, 1H), 6.97 (dd, J = 14.3, 6.9 Hz, 1H), 6.91 (dd, J = 6.8, 4.2 Hz, 3H), 6.83 (t, J = 7.8 Hz, 1H), 5.19 (s, 1H), 1.32 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 180.6, 153.1, 140.2, 135.5, 134.5, 134.1, 129.7, 128.0, 127.3, 125.7, 125.1, 124.8, 122.5, 121.5, 120.3, 119.7, 118.4, 116.5, 110.2, 57.6, 34.4, 30.2; IR (film): γ = 3437, 3241, 3056, 2925, 1706, 1618, 1471, 1256, 1157, 910 cm−1; HRMS (EI-TOF): calcd. for C30H31ClN2O2 486.2074, found 486.2075.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5′-methoxy-3,3′-biindolin-2-one (3g), 92% yield, 1H NMR (400 MHz, CDCl3) δ 8.38 (s, 1H), 8.02 (s, 1H), 7.29 (d, J = 6.4 Hz, 2H), 7.26 (s, 1H), 7.21 (t, J = 7.7 Hz, 1H), 7.16 (d, J = 8.8 Hz, 1H), 7.00 (t, J = 7.5 Hz, 1H), 6.94 (d, J = 7.7 Hz, 1H), 6.82 (d, J = 2.5 Hz, 1H), 6.75 (dd, J = 8.8, 2.4 Hz, 1H), 6.36 (d, J = 2.3 Hz, 1H), 5.17 (s, 1H), 3.53 (s, 3H), 1.33 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 180.3, 153.5, 152.9, 140.0, 135.4, 134.8, 131.9, 130.0, 127.9, 126.4, 125.9, 124.9, 122.5, 116.9, 112.3, 111.8, 109.8, 102.5, 57.5, 55.4, 34.4, 30.2; IR (film): γ = 3337, 3141, 2956, 2870, 1706, 1618, 1471, 1206, 1157, 910, 750, 624 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O3 482.2569, found 482.2570.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-7′-methoxy-3,3′-biindolin-2-one (3h), 90% yield, 1H NMR (400 MHz, CDCl3) δ 9.18 (s, 1H), 8.59–8.20 (m, 1H), 7.29 (s, 1H), 7.22 (d, J = 6.0 Hz, 1H), 7.15 (t, J = 8.2 Hz, 1H), 6.94 (t, J = 7.6 Hz, 1H), 6.88 (d, J = 7.7 Hz, 1H), 6.83 (d, J = 2.5 Hz, 1H), 6.79 (d, J = 7.9 Hz, 1H), 6.61 (d, J = 8.1 Hz, 1H), 6.54 (d, J = 7.7 Hz, 1H), 5.16 (s, 1H), 3.88 (s, 1H), 1.32 (s, 1H); 13C NMR (101 MHz, CDCl3) δ 181.1, 153.0, 145.9, 140.3, 135.3, 135.1, 135.0, 130.1, 127.8, 127.4, 127.2, 125.8, 125.0, 124.1, 122.4, 119.8, 117.6, 113.7, 110.1, 101.9, 57.7, 55.2, 34.5, 30.3; IR (film): γ = 3537, 3241, 3056, 2925, 2870, 1706, 1618, 1236, 1157, 910, 747, 650 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O3 482.2569, found 482.2568.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-methyl-3,3′-biindolin-2-one (3i), 89% yield; 1H NMR (400 MHz, DMSO) δ 10.94 (d, J = 2.0 Hz, 1H), 10.48 (s, 1H), 7.34 (d, J = 8.1 Hz, 1H), 7.17 (s, 2H), 7.04–6.97 (m, 2H), 6.92 (dd, J = 11.4, 6.3 Hz, 3H), 6.86 (d, J = 7.8 Hz, 1H), 6.81 (d, J = 7.3 Hz, 1H), 6.76 (d, J = 2.5 Hz, 1H), 2.19 (s, 3H), 1.28 (s, 18H); 13C NMR (101 MHz, DMSO) δ 179.1, 152.6, 138.8, 138.3, 136.7, 134.7, 131.0, 130.1, 128.0, 125.8, 125.6, 124.7, 124.1, 120.9, 120.2, 118.2, 115.9, 111.5, 109.3, 56.9, 34.5, 30.2, 20.7; IR (film): γ = 3423, 2968, 2254, 1657, 1487, 1435, 1386, 825, 763, 630 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O2 466.2620, found 466.2619.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-4′,5-dimethyl-3,3′-biindolin-2-one (3j), 87% yield; 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.07 (d, J = 1.8 Hz, 1H), 7.12 (d, J = 8.1 Hz, 1H), 7.05 (s, 1H), 6.97 (t, J = 7.5 Hz, 2H), 6.92 (s, 1H), 6.76 (d, J = 7.8 Hz, 1H), 6.71 (d, J = 7.1 Hz, 1H), 6.46 (s, 1H), 2.24 (s, 3H), 1.97 (d, J = 5.4 Hz, 3H), 1.34 (d, J = 4.6 Hz, 18H); 13C NMR (101 MHz, CDCl3) δ 153.0, 138.0, 137.5, 136.0, 131.5, 128.2, 126.9, 124.9, 122.2, 122.1, 109.8, 109.1, 34.6, 30.2, 21.1; IR (film): γ = 3403, 2956, 2925, 1699, 1622, 1464, 1238, 1076, 1016 cm−1; HRMS (EI-TOF): calcd. for C32H36N2O2 480.2777, found 480.2776.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5,5′-dimethyl-3,3′-biindolin-2-one (3k), 91% yield; 1H NMR (400 MHz, CDCl3) δ 8.81 (s, 1H), 8.00 (d, J = 1.6 Hz, 1H), 7.31 (s, 2H), 7.02 (d, J = 3.8 Hz, 2H), 6.96 (d, J = 7.9 Hz, 1H), 6.89 (d, J = 8.2 Hz, 1H), 6.77 (d, J = 7.9 Hz, 1H), 6.72 (dd, J = 5.9, 1.8 Hz, 2H), 5.15 (s, 1H), 2.35 (s, 3H), 2.21 (s, 3H), 1.33 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 181.0, 152.9, 137.7, 137.3, 135.2, 135.0, 131.7, 131.6, 130.2, 128.1, 126.5, 125.0, 124.0, 123.8, 121.2, 120.5, 117.0, 111.1, 109.7, 57.8, 34.5, 30.3, 21.6, 21.2; IR (film): γ = 3627, 3403, 2956, 1701, 1624, 1492, 1390, 1322, 1160, 1096, 1051, 881 cm−1; HRMS (EI-TOF): calcd. for C32H36N2O2 480.2777, found 480.2775.
6′-Bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-3,3′-biindolin-2-one (3l), 85% yield, 1H NMR (400 MHz, CDCl3) δ 8.49 (s, 1H), 8.21 (s, 1H), 7.39 (d, J = 1.6 Hz, 1H), 7.23 (s, 2H), 7.03–6.96 (m, 3H), 6.89 (d, J = 8.6 Hz, 1H), 6.80 (d, J = 8.3 Hz, 1H), 6.75 (d, J = 2.5 Hz, 1H), 5.17 (s, 1H), 2.24 (s, 3H), 1.32 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 180.5, 153.0, 137.7, 137.5, 135.4, 134.6, 132.0, 129.9, 128.4, 126.3, 125.1, 124.8, 124.7, 122.7, 122.4, 117.3, 115.6, 114.1, 109.7, 57.6, 34.4, 30.2, 21.2; IR (film): γ = 3437, 3141, 2956, 2925, 1706, 1618, 1471, 1322, 1157, 1021, 910, 747, 644 cm−1; HRMS (EI-TOF): calcd. for C31H34BrN2O2 545.1804, found 545.1805.
7′-Chloro-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-3,3′-biindolin-2-one (3m), 87% yield, 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 8.28 (s, 1H), 7.27 (s, 2H), 7.11 (d, J = 7.4 Hz, 1H), 7.01 (d, J = 6.9 Hz, 2H), 6.95 (d, J = 8.0 Hz, 1H), 6.91 (d, J = 2.5 Hz, 1H), 6.88–6.79 (m, 1H), 5.18 (s, 1H), 2.25 (s, 3H), 1.33 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 180.3, 153.0, 137.6, 135.4, 134.5, 134.1, 131.9, 129.8, 128.4, 127.4, 126.4, 125.1, 124.9, 121.4, 120.3, 119.8, 118.6, 116.4, 109.7, 57.6, 34.4, 30.2, 21.2. IR (film): γ = 3137, 3041, 2956, 2870, 1706, 1618, 1378, 1322, 1157, 910, 744, 603 cm−1; HRMS (EI-TOF): calcd. for C31H34ClN2O2 501.2309, found 501.2308.
4′-Bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-3,3′-biindolin-2-one (3n), 88% yield, 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.40 (s, 1H), 7.92 (s, 1H), 7.17–7.05 (m, 2H), 7.02 (s, 1H), 6.97 (d, J = 7.9 Hz, 1H), 6.81 (t, J = 7.4 Hz, 2H), 6.70 (d, J = 7.6 Hz, 1H), 6.35 (s, 1H), 5.21 (s, 1H), 2.23 (s, 3H), 1.34 (d, J = 33.0 Hz, 18H); 13C NMR (101 MHz, CDCl3) δ 183.7, 153.1, 138.9, 138.5, 135.9, 135.3, 134.9, 131.0, 130.0, 128.1, 126.4, 125.9, 124.9, 124.7, 122.8, 113.8, 110.7, 110.0, 57.7, 34.6, 30.4, 30.1, 21.2; IR (film): γ = 3537, 3241, 3024, 2956, 2870, 1706, 1471, 1322, 1157, 1021, 910, 747, 644 cm−1; HRMS (EI-TOF): calcd. for C31H34BrN2O2 545.1804, found 545.1805.
5-Chloro-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-4′-methyl-3,3′-biindolin-2-one (3o), 90% yield; 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.28 (s, 1H), 7.27 (s, 2H), 7.11 (d, J = 7.4 Hz, 1H), 7.01 (d, J = 6.9 Hz, 2H), 6.96 (d, J = 8.0 Hz, 1H), 6.92 (d, J = 2.5 Hz, 1H), 6.89–6.79 (m, 1H), 5.18 (s, 1H), 2.25 (s, 3H), 1.33 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 180.3, 153.0, 137.6, 135.4, 134.5, 134.1, 131.9, 129.8, 128.43, 127.4, 126.4, 125.1, 124.8, 121.4, 120.3, 119.8, 118.6, 116.4, 109.7, 57.6, 34.4, 30.2, 21.2; IR (film): γ = 3403, 2955, 2924, 2254, 1714, 1613, 1472, 1435, 1160, 1007, 763, 630 cm−1; HRMS (EI-TOF): calcd. for C31H34ClN2O2 501.2309, found 501.2308.
6′-Bromo-5-chloro-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3,3′-biindolin-2-one (3p), 93% yield; 1H NMR (400 MHz, DMSO) δ 11.17 (d, J = 2.1 Hz, 1H), 10.79 (s, 1H), 7.58 (d, J = 1.7 Hz, 1H), 7.30 (dd, J = 8.3, 2.1 Hz, 1H), 7.11 (d, J = 2.1 Hz, 1H), 7.09 (s, 2H), 7.03–6.99 (m, 3H), 6.94–6.86 (m, 2H), 1.28 (s, 18H); 13C NMR (101 MHz, DMSO) δ 178.6, 152.9, 140.1, 138.7, 137.7, 136.4, 130.1, 127.9, 125.9, 125.5, 124.9, 124.4, 123.8, 121.9, 121.3, 115.1, 114.3, 113.9, 111.3, 57.1, 34.5, 30.2; IR (film): γ = 3628, 3345, 2957, 2925, 1711, 1615, 1436, 1375, 1079, 1021, 1007, 808 cm−1; HRMS (EI-TOF): calcd. for C30H30 BrClN2O2 564.1179, found 564.1179.
5-Bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3,3′-biindolin-2-one (3q), 87% yield; 1H NMR (400 MHz, DMSO) δ 11.02 (d, J = 2.0 Hz, 1H), 10.77 (s, 1H), 7.43 (dd, J = 8.3, 2.0 Hz, 1H), 7.36 (d, J = 8.2 Hz, 1H), 7.20 (d, J = 1.9 Hz, 1H), 7.14 (s, 2H), 7.08–7.02 (m, 2H), 6.96 (d, J = 8.3 Hz, 1H), 6.89 (d, J = 7.9 Hz, 1H), 6.86–6.79 (m, 2H), 1.28 (s, 18H); 13C NMR (101 MHz, DMSO) δ 178.7, 152.9, 140.6, 138.6, 137.0, 136.8, 130.6, 130.1, 127.7, 125.3, 24.8, 123.9, 121.1, 119.8, 118.4, 115.0, 113.1, 111.7, 57.1, 34.6, 30.2; IR (film): γ = 3404, 2983, 2356, 1677, 1472, 1359, 1251, 905, 826, 764 cm−1; HRMS (EI-TOF): calcd. for C30H31 BrN2O3 530.1569, found 530.1572.
5-Bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-4′-methyl-3,3′-biindolin-2-one (3r), 88% yield; 1H NMR (400 MHz, DMSO) δ 10.99 (d, J = 1.9 Hz, 1H), 10.68 (s, 1H), 7.44 (dd, J = 8.2, 1.8 Hz, 1H), 7.23 (d, J = 8.0 Hz, 1H), 7.08 (d, J = 15.5 Hz, 2H), 6.95 (t, J = 7.9 Hz, 3H), 6.63 (d, J = 7.1 Hz, 1H), 6.45 (s, 1H), 1.86 (s, 3H), 1.31 (s, 18H); 13C NMR (101 MHz, DMSO) δ 152.9, 140.4, 138.5, 137.9, 130.6, 127.9, 124.4, 121.3, 121.1, 112.9, 111.9, 109.6, 57.9, 34.6, 30.2; IR (film): γ = 3421, 2924, 2256, 1655, 1472, 1379, 1051, 1005, 826, 764 cm−1; HRMS (EI-TOF): calcd. for C31H33 BrN2O2 544.1725, found 544.1721.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-methyl-3,3′-biindolin-2-one (3s), 92% yield; 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.29 (q, J = 7.9 Hz, 3H), 7.25 (d, J = 1.3 Hz, 1H), 7.22–7.16 (m, 1H), 7.15–7.05 (m, 1H), 7.02 (t, J = 7.2 Hz, 1H), 6.94 (dd, J = 7.6, 4.2 Hz, 2H), 6.91–6.84 (m, 1H), 6.80 (d, J = 2.5 Hz, 1H), 5.14 (s, 1H), 3.32 (s, 3H), 1.32 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 178.2, 152.9, 143.0, 136.9, 135.2, 134.2, 130.1, 127.9, 125.9, 125.6, 124.9, 124.3, 124.1, 122.5, 121.9, 120.8, 120.7, 119.8, 119.4, 117.5, 111.1, 108.1, 102.5, 57.1, 34.5, 30.2, 26.6; IR (film): γ = 3637, 3301, 2956, 2925, 1706, 1471, 1436, 1237, 1143, 909, 803, 750, 668 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O2 466.2620, found 466.2617.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1′-methyl-3,3′-biindolin-2-one (3t), 94% yield; 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.29 (q, J = 7.9 Hz, 3H), 7.25 (d, J = 1.3 Hz, 1H), 7.22–7.16 (m, 1H), 7.15–7.05 (m, 1H), 7.02 (t, J = 7.2 Hz, 1H), 6.94 (dd, J = 7.6, 4.2 Hz, 2H), 6.91–6.84 (m, 1H), 6.80 (d, J = 2.5 Hz, 1H), 5.14 (s, 1H), 3.32 (s, 3H), 1.32 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 178.2, 152.9, 143.0, 136.9, 135.2, 134.2, 130.1, 127.9, 125.9, 125.6, 124.9, 124.3, 124.1, 122.5, 121.9, 120.8, 120.7, 119.7, 119.4, 117.5, 111.1, 108.1, 102.5, 57.1, 34.4, 30.2, 26.6; IR (film): γ = 3637, 3301, 2956, 1706, 1619, 1471, 1321, 1237, 1143, 909, 803, 750 cm−1; HRMS (EI-TOF): calcd. for C31H34N2O2 466.2620, found 466.2617.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-(1H-pyrrol-2-yl)indolin-2-one (3u), 94% yield; 1H NMR (400 MHz, DMSO) δ 10.57 (s, 2H), 7.39 (d, J = 7.4 Hz, 1H), 7.22 (td, J = 7.7, 1.1 Hz, 1H), 7.01 (td, J = 7.6, 0.8 Hz, 1H), 6.95–6.89 (m, 2H), 6.83 (s, 2H), 6.68 (dd, J = 4.3, 2.6 Hz, 1H), 5.91 (dd, J = 5.6, 2.6 Hz, 1H), 5.82 (dd, J = 4.5, 3.0 Hz, 1H), 1.26 (s, 18H); 13C NMR (101 MHz, DMSO) δ 177.9, 152.8, 141.2, 138.5, 133.7, 132.1, 129.3, 127.8, 125.3, 123.6, 121.6, 118.9, 109.5, 107.3, 106.2, 57.3, 34.4, 30.1; IR (film): γ = 3637, 3201, 2956, 1706, 1645, 1540, 1436, 955, 803, 750, 608 cm−1; HRMS (EI-TOF): calcd. for C26H30 N2O2 402.2707, found 402.2701.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-methyl-3-(1H-pyrrol-2-yl)indolin-2-one (3v), 95% yield, 1H NMR (400 MHz, CDCl3) δ 9.00 (s, 1H), 8.71 (dd, J = 28.4, 6.2 Hz, 1H), 7.10 (s, 1H), 7.01 (d, J = 7.9 Hz, 1H), 6.88 (s, 2H), 6.81 (d, J = 8.0 Hz, 2H), 6.13 (dd, J = 5.2, 2.5 Hz, 1H), 6.05 (t, J = 2.8 Hz, 1H), 5.15 (s, 1H), 2.31 (s, 3H), 1.33 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 180.4, 180.4, 153.0, 135.7, 134.0, 132.3, 132.1, 128.4, 126.3, 123.9, 118.6, 109.9, 108.6, 107.7, 57.8, 34.3, 30.2, 21.3. IR (film): γ = 3337, 3141, 3025, 2956, 2870, 1706, 1618, 1471, 1378, 1322, 910, 750, 644 cm−1; HRMS (EI-TOF): calcd. for C27H32N2O2 416.2464, found 416.2464.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-methoxy-3-(1H-pyrrol-2-yl)indolin-2-one (3w), 97% yield, 1H NMR (400 MHz, CDCl3) δ 9.02 (s, 1H), 8.62 (s, 1H), 6.89 (d, J = 2.4 Hz, 1H), 6.87 (s, 2H), 6.84 (d, J = 8.5 Hz, 1H), 6.81 (dd, J = 3.9, 2.4 Hz, 1H), 6.75 (dd, J = 8.5, 2.5 Hz, 1H), 6.14 (dd, J = 5.9, 2.8 Hz, 1H), 6.08 (t, J = 3.5 Hz, 1H), 5.14 (s, 1H), 3.77 (s, 3H), 1.32 (s, 18H); 13C NMR (101 MHz, CDCl3) δ 180.2, 155.9, 153.1, 135.7, 135.3, 133.3, 131.9, 128.2, 123.8, 118.7, 112.9, 112.5, 110.5, 108.6, 107.8, 58.1, 55.8, 34.3, 30.2; IR (film): γ = 3037, 3141, 2956, 2925, 2770, 1706, 1618, 1471, 1436, 1378, 1322, 1236, 1157, 1021, 850, 747, 624 cm−1; HRMS (EI-TOF): calcd. for C27H32N2O3 432.2413, found 432.2414.