Organic & Biomolecular Chemistry
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(CH2Cl2). IR (ATR): 3015 (s), 2221 (m), 2066 (w), 1634 (s), 1512 (s), 1063 (s), 1016 (s). HRMS (DART): calculated for
(s), 1488 (s), 1453 (s), 1262 (m), 1220 (m), 1097 (m), 1030 (w). [C22H16F3NH]+ 352.1313, measured 352.1317.
HRMS (DART): calculated for [C22H19NH]+ 298.1590, measured
298.1581.
2-(Pyridin-3-yl)-1-(p-tolyl)-1H-indole (2g). Column chrom-
atography eluent: hexanes to CH2Cl2, step gradient. Brown
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2-(m-Tolyl)-1-(p-tolyl)-1H-indole (2c). Column chromato- solid (79%). H NMR (500 MHz, CDCl3): δ 8.65–8.62 (m, 1H),
graphy eluent: hexanes to CH2Cl2, step gradient. White solid 8.48–8.44 (m, 1H), 7.72–7.68 (m, 1H), 5.54–5.50 (m, 1H),
(72%). 1H NMR (500 MHz, CDCl3): δ: 7.78–7.74 (m, 1H), 7.27–7.11 (m, 8H), 6.87 (s, 1H), 2.42 (s, 3H). 13C NMR
7.37–7.34 (m, 1H), 7.30–7.16 (m, 8H), 7.13–7.07 (m, 2H), 6.87 (126 MHz, CDCl3): δ 149.5, 148.1, 139.7, 137.6, 137.2, 135.6,
(d, J = 0.8 Hz), 2.47 (s, 3H), 2.36 (s, 3H). 13C NMR (126 MHz, 135.5, 130.0, 128.9, 128.2, 122.7, 120.8, 120.7, 110.7, 104.4,
CDCl3): δ 141.0, 139.2, 137.8, 137.0, 136.0, 132.6, 129.9, 129.7, 20.9. TLC: Rf = 0.6 (CH2Cl2). IR (ATR): 3029 (m), 2920 (m), 1920
128.3, 128.1, 128.0, 127.9, 126.1, 122.2, 120.6, 120.5, 110.7, (w), 1771 (w), 1697 (w), 1661 (w), 1607 (m), 1571 (m), 1555 (w),
103.4, 21.5, 21.2. TLC: Rf = 0.5 (CH2Cl2). IR (ATR): 3031 (m), 1541 (w), 1535 (w), 1510 (s), 1448 (s), 1421 (m), 1376 (m), 1364
2920 (m), 2862 (w), 1880 (w), 1606 (s), 1510 (s), 1483 (w), 1452 (m), 1350 (m), 1324 (m), 1310 (m), 1254 (m), 1208 (m), 1173
(s), 1376 (m), 1352 (m), 1316 (m), 1274 (w), 1261 (w), 1211 (m), (m), 1143 (w), 1127 (w), 1108 (w), 1104 (m), 1038 (w), 1024 (m),
1173 (w), 1147 (w), 1108 (w), 1095 (w), 1078 (w), 1039 (w), 1014 1016 (m). HRMS (DART): calculated for [C20H16N2H]+
(w). HRMS (DART): calculated for [C22H19NH]+ 298.1590, 285.1386, measured 285.1362.
measured 298.1598.
4-(1-(p-Tolyl)-1H-indol-2-yl)benzonitrile
(2h). Column
1,2-di-p-Tolyl-1H-indole
(2d). Column
chromatography chromatography eluent: CH2Cl2 to MeOH–CH2Cl2, 1/39, step
eluent: hexanes to CH2Cl2–hexanes, 4/6, step gradient. White gradient. Off-white solid (80%). 1H NMR (500 MHz, CDCl3):
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solid (69%). H NMR (500 MHz, CDCl3): δ 7.74–7.70 (m, 1H), δ 7.72–7.68 (m, 3H), 7.38–7.34 (dt, J = 8.8 Hz, 2 Hz, 2H),
7.33–7.29 (m, 1H), 7.28–7.17 (m, 8H), 7.12–7.09 (d, J = 8 Hz, 7.30–7.28 (m, 1H), 7.25–7.22 (m, 2H), 7.22–7.17 (m, 2H),
2H) 6.81 (d, J = 0.6 Hz, 1H), 2.45 (s, 3H), 2.36 (s, 3H). 13C NMR 7.15–7.12 (m, 2H), 6.89 (d, J = 0.8 Hz), 2.42 (s, 3H). 13C NMR
(126 MHz, CDCl3): δ 140.9, 139.1, 137.1, 137.0, 136.0, 129.9, (126 MHz, CDCl3): δ 168.9, 139.5, 137.4, 136.3, 135.6, 131.6,
129.8, 128.9, 128.8, 128.3, 127.9, 122.0, 120.5, 120.4, 110.7, 130.1, 128.7, 128.0, 127.7, 127.7, 122.9, 120.8, 120.7, 110.8,
103.0, 21.2, 21.2. TLC: Rf = 0.2 (hexanes). IR (ATR): 3029 (m), 104.5, 21.2. TLC: Rf = 0.1 (CH2Cl2), 0.4 (MeOH–CH2Cl2, 1/39).
2960 (m), 1844 (w), 1749 (w), 1716 (w), 1699 (w), 1674 (w), IR (ATR): 3480 (m), 3365 (w), 3149 (s), 2922 (w), 1905 (w), 1793
1606 (w), 1555 (w), 1542 (m), 1513 (s), 1500 (m), 1455 (s), (w), 1680 (s), 1663 (s), 1605 (s), 1563 (m), 1541 (w), 1535 (w),
1412 (w), 1380 (m), 1357 (m), 1320 (w), 1307 (m), 1255 (w), 1472 (w), 1453 (m), 1411 (w), 1380 (s), 1352 (m), 1321 (m), 1282
1187 (w), 1174 (w), 1147 (w), 1113 (w), 1021 (w). HRMS (m), 1259 (m), 1210 (m), 1139 (m), 1106 (m), 1017 (m). HRMS
(DART): calculated for [C22H19NH]+ 298.1590, measured (DART): calculated for [C22H16N2H]+ 309.1386, measured
298.1573.
309.1380.
2-(4-(tert-Butyl)phenyl)-1-(p-tolyl)-1H-indole (2e). Column
2-(tert-Butyl)-1-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine
(2j).
chromatography eluent: hexanes to CH2Cl2–hexanes, 1/1, step Column chromatography eluent: hexanes to CH2Cl2, step gra-
gradient. White solid (67%). 1H NMR (500 MHz, CDCl3): δ dient. Brown solid (68%). 1H NMR (500 MHz, CDCl3):
7.73–7.68 (m, 1H), 7.32–7.23 (m, 7H), 7.21–7.16 (m, 4H), 6.81 δ 8.22–8.19 (dd, J = 4.7 Hz, 1.5 Hz, 1H), 7.86–7.83 (dd, J = 7.8 Hz,
(d, J = 0.8 Hz, 1H), 2.45 (s, 3H), 1.33 (s, 9H). 13C NMR 1.5 Hz, 1H), 7.34–7.31 (d, J = 2 Hz, 2H), 7.29–7.25 (m, 2H),
(126 MHz, CDCl3): δ 150.2, 140.8, 139.2, 137.0, 136.1, 129.9, 7.04–7.00 (dd, J = 8 Hz, 4.5 Hz, 1H), 6.41 (s, 1H), 2.46 (s, 3H),
129.6, 128.4, 128.3, 127.9.2, 125.0, 122.0, 120.5, 120.3, 110.7, 1.29 (s, 9H). 13C NMR (126 MHz, CDCl3): δ 151.6, 151.2, 142.8,
103.0, 34.5, 31.3, 21.2. TLC: Rf = 0.2 (hexanes). IR (ATR): 3031 138.7, 136.2, 130.5, 129.7, 127.3, 119.5, 116.0, 96.9, 33.5, 30.7,
(w), 2960 (m), 2864 (w), 1844 (w), 1734 (w), 1716 (w), 1699 (w), 21.4. TLC: Rf = 0.6 (CH2Cl2), 0.7 (MeOH–CH2Cl2, 1/19), 0.2
1675 (w), 1606 (w), 1564 (w), 1555 (w), 1541 (w), 1535 (w), 1513 (CH2Cl2–hexanes, 1/1). IR (ATR): 3041 (m), 2958 (s), 2924 (s),
(s), 1503 (m), 1473 (w), 1409 (w), 1378 (m), 1360 (w), 1347 (m), 2869 (s), 1593 (m), 1574 (m), 1525 (s), 1515 (s), 1470 (m),
1321 (m), 1259 (m), 1200 (m), 1175 (w), 1113 (m), 1017 (m). 14 010 (s), 1393 (m), 1361 (s), 1311 (s), 1285 (s), 1246 (s),
HRMS (DART): calculated for [C25H25NH]+ 340.2060, measured 1216 (m), 1199 (m), 1132 (w), 1107 (m), 1041 (w), 1023 (w).
340.2037.
HRMS (DART): calculated for [C18H20N2H]+ 265.1705,
1-(p-Tolyl)-2-(4-(trifluoromethyl)phenyl)-1H-indole
(2f). measured 265.1703.
Column chromatography eluent: hexanes to CH2Cl2–hexanes
1-(p-Tolyl)-1H-pyrrolo[2,3-b]pyridine (2k). Column chrom-
1/1, step gradient. White solid (81%). 1H NMR (500 MHz, atography eluent: hexanes to CH2Cl2–hexanes 1/1, step gradi-
CDCl3): δ 7.72–7.49 (m, 1H), 7.53–7.38 (d, J = 8.5 Hz, 2H), ent. Brown solid (51%). 1H NMR (500 MHz, CDCl3):
7.30–7.17 (m, 7H), 7.16–7.12 (dt, J = 8.5 Hz, 2 Hz, 2H). 6.88 (d, δ 8.39–8.36 (d, J = 4.5 Hz, 1H), 7.99–7.96 (d, J = 9 Hz), 7.64–7.61
J = 0.7 Hz), 2.45 (s, 3H). 13C NMR (126 MHz, CDCl3): δ 139.5, (d, J = 8 Hz, 2H), 7.51–7.48 (d, J = 3.5 Hz, 1H), 7.35–7.32 (d, J =
139.0, 137.5, 136.1, 135.5, 130.2, 128.8, 128.0, 127.7, 125.1 (q, 8.5 Hz, 2H), 7.15–7.11 (ddd, J = 8.0 Hz, 4.5 Hz, 0.7 Hz, 1H),
J = 3.8 Hz), 123.1, 122.9, 120.8 (d, J = 12.6 Hz), 110.8, 104.7, 6.63–6.61 (dd, 3.8 Hz, 0.7 Hz, 1H), 2.43 (s, 3H). 13C NMR
29.7, 21.1. TLC: Rf = 0.3 (hexanes). IR (ATR): 3034 (m), 2920 (126 MHz, CDCl3): δ 143.5, 136.2, 135.9, 129.9, 128.0, 124.0,
(m), 1617 (s), 1514 (s), 1474 (w), 1453 (s), 1412 (m), 1379 (m), 116.5, 108.2, 107.7, 101.2, 21.0. TLC: Rf = 0.8 (CH2Cl2), 0.4
1320 (s), 1257 (w), 1212 (m), 1165 (s), 1123 (s), 1109 (s), 1079 (CH2Cl2–hexanes, 1/1). IR (ATR): 2923 (s), 1594 (s), 1530 (s),
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