N. T. Patil, A. Konala
FULL PAPER
7.12–7.09 (m, 1 H), 7.02 (t, J = 6.0 Hz, 1 H), 3.78 (t, J = 6.0 Hz, 7.5 Hz, 1 H), 7.07 (d, J = 6.8 Hz, 1 H), 7.00 (d, J = 6.8 Hz, 1 H),
2 H), 2.88 (t, J = 6.0 Hz, 2 H), 2.39 (s, 3 H) ppm. 13C NMR
5.95–5.82 (m, 1 H), 5.08 (d, J = 10.5 Hz, 1 H), 4.78 (d, J = 18.1 Hz,
(75 MHz, CDCl3): δ = 135.0, 133.9, 128.6, 121.3, 119.8, 117.5, 1 H), 4.65–4.62 (m, 2 H), 3.75 (t, J = 6.0 Hz, 2 H), 2.94 (t, J =
111.2, 107.6, 62.6, 27.6, 11.8 ppm. IR (film): ν
= 3410, 2932,
6.0 Hz, 2 H), 2.33 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ =
˜
max
1726, 1623, 1573, 1482, 1452, 1364, 1324, 1230, 1169, 1124, 1056,
743, 589, 520, 432 cm–1. MS (ESI): m/z = 210 [M+ + H]. HRMS:
calcd. for C11H13ClNO [M+ + H] 210.0686; found 210.0682.
136.2, 133.9, 133.5, 127.9, 120.9, 119.1, 117.9, 116.2, 109.0, 107.2,
62.9, 45.4, 28.0, 10.1 ppm. IR (film): νmax = 3392, 3055, 2922, 1620,
˜
1462, 1430, 1340, 1302, 1192, 1136, 1040, 1008, 740, 586, 508,
432 cm–1. MS (ESI): m/z = 216 [M+ + H]. HRMS: calcd. for
C14H18NO [M+ + H] 216.1388; found 216.1380.
2-(1-Benzyl-2methyl-1H-3-indolyl)-1-ethanol (3l):[27] Yield 80 mg
(85%); viscous oil; Rf = 0.62 (hexane/EtOAc, 60:40). 1H NMR
(300 MHz, CDCl3): δ = 7.51–7.48 (m, 1 H), 7.26–7.13 (m, 4 H),
7.00–7.09 (m, 2 H), 6.90 (d, J = 6.8 Hz, 2 H), 5.28 (s, 2 H), 3.80
(t, J = 6.0 Hz, 2 H), 2.98 (t, J = 6.0 Hz, 2 H), 2.31 (s, 3 H) ppm.
13C NMR (75 MHz, CDCl3): δ = 137.8, 136.6, 134.0, 128.7, 127.2,
125.9, 121.0, 119.2, 117.9, 109.0, 107.4, 62.9, 46.5, 28.0, 10.3 ppm.
2-(5-Bromomethyl-1H-3-indolyl)-1-ethanol (3f): Yield 72 mg (80%);
viscous oil; Rf = 0.71 (hexane/EtOAc, 60:40). 1H NMR (300 MHz,
CDCl3): δ = 7.80 (br. s, 1 H), 7.59 (d, J = 8.3 Hz, 1 H), 7.15 (m, 1
H), 7.05 (d, J = 8.3 Hz, 1 H), 4.17 (t, J = 6.8 Hz, 2 H), 2.94 (t, J
= 6.8 Hz, 2 H), 2.39 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ
= 133.7, 130.7, 130.2, 123.7, 120.5, 116.5, 112.4, 111.6, 64.4, 23.6,
11.6 ppm. IR (film): ν
= 3402, 3058, 2928, 1635, 1582, 1482,
˜
max
1450, 1379, 1221, 1168, 1102, 1023, 748, 600, 432 cm–1. MS (ESI):
m/z = 254 [M+ + H]. HRMS: calcd. for C11H13BrNO [M+ + H]
254.0181; found 254.0176.
IR (film): ν
= 3408, 3058, 2926, 1704, 1628, 1575, 1480, 1448,
˜
max
1376, 1218, 1164, 1100, 1020, 746, 582, 430 cm–1. MS (ESI): m/z =
266 [M+ + H]. HRMS: calcd. for C18H20NO [M+ + H] 266.1545;
found 266.1540.
2-(5-Fluoromethyl-1H-3-indolyl)-1-ethanol (3g): Yield 56 mg (82%);
viscous oil; Rf = 0.48 (hexane/EtOAc, 60:40). 1H NMR (300 MHz,
CDCl3): δ = 7.90 (br. s, 1 H), 7.09 (d, J = 3.7 Hz, 1 H), 7.06 (d, J
= 3.7 Hz, 1 H), 6.78 (t, J = 6.8 Hz, 1 H), 3.77 (t, J = 6.0 Hz, 2 H),
2.87 (t, J = 6.0 Hz, 2 H), 2.36 (s, 3 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 160.1, 159.4, 132.6, 131.7, 128.5, 122.0, 115.7, 112.9,
2-Methyl-3-propyl-1H-indole (3m):[28] Yield 51 mg (82%); viscous
oil; Rf = 0.80 (hexane/EtOAc, 90:10). 1H NMR (300 MHz, CDCl3):
δ = 7.57 (br. s, 1 H), 7.42 (d, J = 6.8 Hz, 1 H), 7.13 (d, J = 6.8 Hz,
1 H), 7.04–6.95 (m, 2 H), 2.63 (t, J = 7.5 Hz, 2 H), 2.32 (s, 3 H),
1.69–1.57 (m, 2 H), 0.93 (t, J = 7.5 Hz, 3 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 135.0, 129.4, 128.5, 120.6, 118.7, 117.9,
110.7, 108.9, 103.2, 102.9, 62.7, 27.7, 11.8 ppm. IR (film): ν
=
˜
max
3409, 3055, 2924, 1706, 1655, 1584, 1485, 1451, 1387, 1304, 1231,
1178, 1104, 1042, 958, 848, 795, 602, 434 cm–1. MS (ESI): m/z =
194 [M+ + H]. HRMS: calcd. for C11H13FNO [M+ + H] 194.0981;
found 194.0978.
109.7, 109.2, 31.6, 23.9, 13.9, 11.5 ppm. IR (film): ν
= 3476,
˜
max
3054, 2957, 2925, 2864, 1649, 1458, 1300, 1223, 1153, 1012, 741,
660, 587 cm–1. MS (ESI): m/z = 174 [M+ + H]. HRMS: calcd. for
C12H16N [M+ + H] 174.1283; found 174.1288.
2-(7-Iodo-2-methyl-1H-3-indolyl)-1-ethanol (3h): Yield 94 mg
(88%); viscous oil; Rf = 0.55 (hexane/EtOAc, 60:40). 1H NMR
(300 MHz, CDCl3): δ = 7.84 (br. s, 1 H), 7.41 (m, 2 H), 6.80 (t, J
= 7.5 Hz, 1 H), 3.79 (t, J = 6.0 Hz, 2 H), 2.89 (t, J = 6.0 Hz, 2 H),
2.45 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 138.5, 132.9,
131.2, 129.6, 121.0, 118.0, 109.3, 105.9, 62.7, 27.9, 11.8 ppm. IR
2-Methyl-3-pentyl-1H-indole (3n): Yield 67 mg (94%); viscous oil;
1
Rf = 0.82 (hexane/EtOAc, 90:10). H NMR (300 MHz, CDCl3): δ
= 7.58 (br. s, 1 H), 7.41 (d, J = 6.8 Hz, 1 H), 7.13 (d, J = 6.8 Hz,
1 H), 7.03–6.95 (m, 2 H), 2.64 (t, J = 6.8 Hz, 2 H), 2.32 (s, 3 H),
1.60 (pseudo-t, J = 6.8, 7.6 Hz, 2 H), 1.33–1.27 (m, 4 H), 0.88 (t,
J = 6.8 Hz, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 135.3,
129.7, 128.7, 120.8, 119.0, 118.2, 110.0, 109.5, 31.8, 30.5, 24.2, 22.7,
(film): νmax = 3402, 2924, 1624, 1463, 1345, 1323, 1196, 1140, 1048,
˜
1008, 743, 586, 512, 430 cm–1. MS (ESI): m/z = 302 [M+ + H].
HRMS: calcd. for C11H13INO [M+ + H] 302.0042; found 302.0038.
14.2, 11.7 ppm. IR (film): ν
= 3473, 3042, 2932, 2922, 2856,
˜
max
2-(1,2-Dimethyl-1H-3-indolyl)-1-ethanol (3i):[13] Yield 58 mg (86%);
viscous oil; Rf = 0.70 (hexane/EtOAc, 60:40). 1H NMR (300 MHz,
CDCl3): 7.44 (d, J = 7.5 Hz, 1 H), 7.16 (d, J = 7.5 Hz, 1 H), 7.08
(d, J = 8.3 Hz, 1 H), 7.00 (d, J = 8.3 Hz, 1 H), 3.75 (t, J = 6.0 Hz,
2 H), 3.65 (s, 3 H), 2.94 (t, J = 6.0 Hz, 2 H), 2.37 (s, 3 H) ppm.
13C NMR (75 MHz, CDCl3): δ = 136.6, 134.2, 127.7, 120.7, 118.9,
1638, 1446, 1320, 1234, 1158, 1029, 734, 623, 524 cm–1. MS (ESI):
m/z = 202 [M+ + H]. HRMS: calcd. for C14H20N [M+ + H]
202.1596; found 202.1590.
3-Benzyl-2-methyl-1H-indole (3o):[29] Yield 70 mg (89%); viscous
oil; Rf = 0.76 (hexane/EtOAc, 90:10). 1H NMR (300 MHz, CDCl3):
δ = 7.70 (br. s, 1 H), 7.29–7.32 (m, 1 H), 7.19–7.13 (m, 5 H), 7.11–
7.08 (m, 1 H), 7.05–6.92 (m, 2 H), 4.03 (s, 2 H), 2.37 (s, 3 H) ppm.
13C NMR (75 MHz, CDCl3): δ = 141.7, 131.7, 130.4, 128.6, 128.3,
126.8, 125.7, 120.9, 119.2, 118.4, 112.4, 110.2, 45.2, 11.8 ppm. IR
117.8, 108.6, 106.6, 62.9, 29.5, 27.9, 10.3 ppm. IR (film): ν
=
˜
max
3396, 3048, 2924, 1615, 1470, 1433, 1367, 1329, 1243, 1185, 1039,
883, 737, 558 cm–1. MS (ESI): m/z = 190 [M+ + H]. HRMS: calcd.
for C12H16NO [M+ + H] 190.1231; found 190.1236.
(film): νmax = 3403, 3052, 2952, 2864, 1649, 1457, 1432, 1322, 1190,
˜
1132, 1041, 1002, 740, 586, 506, 430 cm–1. MS (ESI): m/z = 222
[M+ + H]. HRMS: calcd. for C16H16N [M+ + H] 222.1283; found
222.1278.
Benzyl 3-(2-Hydroxyethyl)-2-methyl-1H-1-indolecarboxylate (3j):
Yield 84 mg (76%); viscous oil; Rf = 0.68 (hexane/EtOAc, 60:40).
1H NMR (300 MHz, CDCl3): δ = 7.48 (d, J = 1.5 Hz, 1 H), 7.46
(d, J = 1.5 Hz, 1 H), 7.42–7.34 (m, 5 H), 7.18–7.15 (m, 2 H), 5.44
(s, 2 H), 3.78 (t, J = 6.0 Hz, 2 H), 2.91 (t, J = 6.0 Hz, 2 H), 2.57
(s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 157.1, 132.4, 130.4,
129.1, 128.8, 128.7, 128.6, 128.4, 123.8, 122.8, 117.8, 115.7, 68.6,
3-(2-Methyl-1H-3-indolyl)-1-propanol (3p):[30] Yield 62 mg (92%);
viscous oil; Rf = 0.52 (hexane/EtOAc, 60:40). 1H NMR (300 MHz,
CDCl3): δ = 7.65 (br. s, 1 H), 7.42 (d, J = 8.3 Hz, 1 H), 7.14 (d, J
= 8.3 Hz, 1 H), 7.04–6.98 (m, 2 H), 3.59 (t, J = 6.2 Hz, 2 H), 2.75
(d, J = 7.3 Hz, 2 H), 2.33 (s, 3 H), 1.85 (pent, J = 6.2, 7.3 Hz, 2
H) ppm. 13C NMR (75 MHz, CDCl3): δ = 135.2, 130.9, 128.5,
120.7, 118.9, 117.8, 111.0, 110.2, 62.4, 33.2, 20.1, 11.4 ppm. IR
62.2, 27.5, 11.2 ppm. IR (film): ν
= 3386, 3045, 2924, 1618,
˜
max
1460, 1430, 1342, 1192, 1130, 1040, 1007, 740, 586, 508, 430 cm–1.
MS (ESI): m/z = 310 [M+ + H]. HRMS: calcd. for C19H20NO3 [M+
+ H] 310.1443; found 310.1438.
(film): νmax = 3385, 3045, 2920, 1611, 1452, 1423, 1323, 1305, 1185,
˜
2-(1-Allyl-2-methyl-1H-3-indolyl)-1-ethanol (3k): Yield 61 mg
(80%); viscous oil; Rf = 0.65 (hexane/EtOAc, 60:40). 1H NMR
(300 MHz, CDCl3): δ = 7.45 (d, J = 7.5 Hz, 1 H), 7.13 (d, J =
1128, 1022, 1002, 728, 569, 502, 428 cm–1. MS (ESI): m/z = 190
[M+ + H]. HRMS: calcd. for C12H16NO [M+ + H] 190.1232; found
190.1228.
6836
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Eur. J. Org. Chem. 2010, 6831–6839