Maurizio Taddei et al.
2929, 2852, 1597, 1500, 1456, 1378, 1225 cmÀ1 1H NMR
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131.2, 128.8, 128.6, 126.6 (2C), 125.9, 124.6, 123.8, 121.4,
120.4, 120.3 (2C), 118.9, 118.3, 117.2, 109.2, 107.0, 47.9, 47.8,
36.9, 36.8, 22.0, 20.4, 20.3, 18.3, 15.6, 14.7; anal. calcd. for
C19H21N: C 86.64, H 8.04, N 5.32; found: C 86.62, H 8.09, N
5.29.
;
(400 MHz, CDCl3): d=7.65 (ddd, J1 =7.7 Hz, J2 =1.3 Hz,
J3 =0.8 Hz, 1H), 7.56 (dt, J1 =8.1 Hz, J2 =0.9 Hz, 1H), 7.51–
7.48 (m, 4H), 7.30 (ddd, J1 =8.7 Hz, J2 =4.7, J3 =3.9 Hz,
1H), 7.23–7.13 (m, 3H), 2.84 (qd, J1 =7.5 Hz, J2 =1.1 Hz,
2H), 1.38 (t, J=7.5 Hz, 3H); 13C NMR (100 MHz, CDCl3):
d=140.1, 136.1, 129.6, 129.0, 125.9, 124.4, 124.1, 122.4, 119.9,
119.7, 119.3, 110.5, 18.3, 14.4. These assignments matched
with those previously published.[39]
3-Ethyl-5-methoxy-1-phenethyl-1H-indole (18): Light
yellow oil; yield: 260 mg (93%); Rf 0.65 (hexane/AcOEt:
8/2). IR (film): n=3062, 3027, 2960, 2246, 1619, 1603, 1578,
1487, 1453, 1360, 1222 cmÀ1 1H NMR (400 MHz, CDCl3):
;
d=7.28–7.16 (m, 4H), 7.09–7.03 (m, 3H), 6.86 (dd, J1 =
8.8 Hz, J2 =2.5 Hz, 1H), 6.69 (s, 1H), 4.22 (t, J=7.5 Hz,
2H), 3.86 (d, J=5.0 Hz, 3H), 3.04 (t, J=7.5 Hz, 2H), 2.70
(q, J=7.5 Hz, 2H), 1.27 (t, J=7.5 Hz, 3H); 13C NMR
(100 MHz, CDCl3): d=153.6, 138.8, 131.6, 128.8, 128.6,
128.3, 126.6, 125.1, 116.8, 111.6, 110.0, 101.2, 56.0, 48.2, 37.0,
18.3, 14.6; anal. calcd. for C19H21NO: C 81.68, H 7.58, N
5.01; found: C 81.72, H 7.61, N 4.93.
1-Benzyl-3-ethyl-1H-indole (24): Pale yellow oil; yield:
200 mg (85%); Rf 0.54 (hexane/AcOEt: 96/4); IR (film): n=
3059, 3028, 2960, 2930, 2875, 1610, 1495, 1480, 1465, 1450,
1
1355, 1175, 806, 735 cmÀ1; H NMR (400 MHz, CDCl3): d=
7.63–7.61 (m, 1H), 7.30–7.23 (m, 4H), 7.13 (dq, J1 =16.2 Hz,
J2 =8.1 Hz, 4H), 6.89 (s, 1H), 5.27 (s, 2H), 2.79 (q, J=
7.5 Hz, 2H), 1.32 (t, J=7.5 Hz, 3H); 13C NMR (100 MHz,
CDCl3): d=137.9, 136.8, 128.7, 128.0, 127.5, 126.8, 124.7,
121.6, 119.1, 118.7, 118.0, 109.5, 49.8, 18.2, 14.6. These as-
signments matched with those previously published.[40]
1-Butyl-3-pentyl-1H-indole (25): Light yellow oil; yield:
219 mg (90%); Rf 0.7 (hexane/AcOEt: 98/2); IR (neat): n=
3-Methyl-1-phenethyl-1H-indole (19): Amber oil; yield:
221 mg (94%); Rf 0.44 (hexane/AcOEt: 98/2); IR (film): n=
3028, 2959, 1601, 1550, 1498, 1464, 1359, 1182 cmÀ1
;
1H NMR (400 MHz, CDCl3): d=7.61–7.58 (m, 1H), 7.34–
7.20 (m, 5H), 7.16–7.10 (m, 3H), 6.78 (d, J=1.0 Hz, 1H),
4.30 (dd, J1 =8.2 Hz, J2 =7.0 Hz, 2H), 3.09 (t, J=7.6 Hz,
2H), 2.32 (t, J=1.2 Hz, 3H); 13C NMR (100 MHz, CDCl3):
d=138.7, 136.1, 128.7, 128.6, 126.6, 125.4, 121.3, 119.0, 118.6,
110.2, 109.0, 107.5, 47.8, 36.9, 9.5; anal. calcd. for C17H17N: C
86.77, H 7.28, N 5.95; found: C 86.74, H 7.25, N 6.01.
2956, 2927, 2871, 1467, 1370 cmÀ1
;
1H NMR (400 MHz,
CDCl3): d=7.59 (dt, J1 =8 Hz, J2 =0.8 Hz, 1H), 7.29 (d, J=
8.2 Hz, 1H), 7.18 (td, J=7.6 Hz, J2 =1.1 Hz, 1H), 7.07 (ddd,
J1 =7.9 Hz, J2 =7.0 Hz, J3 =0.9 Hz, 1H), 6.86 (s, 1H), 4.06 (t,
J=7.1 Hz, 2H), 2.73 (td, J1 =7.7 Hz, J2 =0.4 Hz, 2H), 1.83–
1.76 (m, 2H), 1.72–1.68 (m, 2H), 1.40–1.30 (m, 6H), 0.95–
0.88 (m, 6H); 13C NMR (100 MHz, CDCl3): d=136.3, 128.1,
124.9, 121.1, 119.2, 118.3, 115.5, 109.2, 45.9, 32.4, 31.9, 30.1,
25.1, 22.6, 20.3, 14.1, 13.8; anal. calcd. for C17H25N: C 83.90,
H 10.35, N 5.75; found: C 83.82, H 10.39, N 5.79.
1-Butyl-3-methyl-1H-indole (20): Colourless oil; yield:
178 mg (95%); Rf 0.55 (hexane/AcOEt: 98/2); IR (film): n=
3053, 2957, 2929, 1467, 1362 cmÀ1
;
1H NMR (400 MHz,
CDCl3): d=7.55 (dt, J=7.9 Hz, 0.9 Hz, 1H), 7.27 (dt, J1 =
8.2, J2 =0.8 Hz, 1H), 7.18 (ddd, J1 =8.2, J2 =7.0 Hz, J3 =
1.2 Hz, 1H), 7.08 (ddd, J1 =7.9 Hz, J2 =6.9 Hz, J3 =1.0 Hz,
1H), 6.83 (d, J=0.9 Hz, 1H), 4.01 (t, J=7.1 Hz, 2H), 2.31
(d, J=1.0 Hz, 3H), 1.76 (dt, J=14.7 Hz, J2 =7.4 Hz, 2H),
1.31 (dq, J=15.1 Hz, 7.5 Hz, 2H), 0.91 (t, J=7.4 Hz, 3H);
13C NMR (100 MHz, CDCl3): d=136.3, 128.6, 125.4, 121.2,
118.9, 118.3, 109.9, 109.1, 45.7, 32.4, 20.2, 13.7, 9.6. These as-
signments matched with those previously published.[36]
1-Benzyl-3-phenyl-1H-indole (26): Colorless crystals,
yield: 227 mg (80%); mp 62–638C [lit.[41] 61–638C]; Rf 0.49
(hexane/AcOEt: 9/1); IR (film): n=3108, 1613, 1483, 1461,
1365, 1344, 1270, 1194 cmÀ1 1H NMR (400 MHz, CDCl3):
;
d=7.97 (dd, J1 =6.9 Hz, J2 =1.4 Hz, 1H), 7.66 (dd, J1 =8.2,
J2 =1.2 Hz, 2H), 7.42 (t, J=7.7 Hz, 2H), 7.33–7.15 (m,
10H), 5.34 (s, 2H); 13C NMR (100 MHz, CDCl3): d=137.2,
137.1, 135.6, 128.9, 128.8, 127.8, 127.4, 127.0, 126.5, 125.9,
125.9, 122.2, 120.2, 120.10, 117.4, 110.1, 50.2. These assign-
ments matched with those previously published.[42]
3-Ethyl-1-methyl-1H-indole (21): Clear oil; yield: 153 mg
(96%); Rf 0.42 (hexane/AcOEt: 98/2).;IR (film): n=3053,
2962, 2929, 1472, 1376 cmÀ1
;
1H NMR (400 MHz, CDCl3):
3-Benzyl-1-butyl-1H-indole (27): Pale yellow oil; yield:
219 mg (83%); Rf 0.32 (hexane/AcOEt: 98/2); IR (neat): n=
d=7.59 (dt, J=7.9, 0.9 Hz, 1H), 7.29–7.27 (m, 1H), 7.21
(ddd, J1 =8.1, J2 =7.0 Hz, J3 =1.1 Hz, 1H), 7.09 (ddd, J1 =
7.9, J2 =6.9, J3 =1.0 Hz, 1H), 6.82 (s, 1H), 3.74 (s, 3H), 2.78
(qd, J1 =7.5, J2 =0.9 Hz, 2H), 1.32 (t, J=7.5 Hz, 3H);
13C NMR (100 MHz, CDCl3): d=137.1, 127.8, 125.4, 121.4,
119.0, 118.4, 117.3, 109.1, 32.5, 18.3, 14.7. These assignments
matched with those previously published.[37]
3057, 3025, 2957, 2929, 2871, 1595, 1494, 1481, 1467 cmÀ1
;
1H NMR (400 MHz, CDCl3): d=7.50 (d, J=7,.9 Hz, 1H),
7.31–7.24 (m, 5H), 7.20–7.16 (m, 2H), 7.04 (td, J=7.5 Hz,
0.9 Hz, 1H), 6.80 (s, 1H), 4.10 (s, 2H), 4.05 (t, J=7.1 Hz,
2H), 1.82–1.74 (m, 2H), 1.33 (dd, J=15.1 Hz, 7.5 Hz, 2H),
0.92 (t, J=7.4 Hz, 3H); 13C NMR (101 MHz, CDCl3): d=
141.5, 136.5, 128.7, 128.3, 127.9, 126.1, 125.8, 121.4, 119.3,
118.7, 114.1, 109.3, 46.0, 32.4, 31.6, 20.3, 13.8; anal. calcd. for
C19H21N: C 86.64, H 8.04, N 5.32; found: C 86.62, H 8.00, N
5.38.
1,3-Diethyl-1H-indole (22): Clear oil; yield: 168 mg
(97%); Rf 0.58 (hexane/AcOEt: 9/1); IR (film): n=3052,
2964, 2930, 1613, 1469, 1370, 1225, 736 cmÀ1 1H NMR
;
(400 MHz, CDCl3): d=7.59 (dd, J1 =7.9 Hz, J2 =0.7 Hz,
1H), 7.30 (d, J=8.2 Hz, 1H), 7.19 (ddd, J1 =8.2 Hz, J2 =
7.0 Hz, J3 =1.1 Hz, 1H), 7.08 (td, J=7.4, 0.9 Hz, 1H), 6.88
(s, 1H), 4.11 (q, J=7.3 Hz, 2H), 2.78 (qd, J1 =7.5, J2 0.9 Hz,
2H), 1.43 (t, J=7.3 Hz, 3H), 1.32 (t, J=7.5 Hz, 3H);
13C NMR (100 MHz, CDCl3): d=136.1, 127.9, 123.6, 121.3,
119.2, 118.4, 117.4, 109.2, 40.7, 18.4, 15.5, 14.7. These assign-
ments matched with those previously published.[38]
9-Methyl-2,3,4,9-tetrahydro-1H-carbazole (28): Colourless
solid after 5 h; yield: 150 mg (81%); mp 41–428C (lit.[43]: mp
40–418C); Rf 0.67 (hexane/AcOEt: 9/1); IR (film): n=3027,
2930, 2845, 1616, 1470, 1418, 1380, 1302, 1247, 1181,
732 cmÀ1
;
1H NMR (400 MHz, CDCl3): d=7.46 (d, J=
7.7 Hz, 1H), 7.25 (t, J=4.0 Hz, 1H), 7.14 (td, J1 =7.6 Hz,
J2 =1.0 Hz, 1H), 7.08–7.04 (m, 1H), 3.61 (s, 3H), 2.74–2.71
(m, 4H), 1.97–1.92 (m, 2H), 1.88–1.83 (m, 2H); 13C NMR
(100 MHz, CDCl3): d=136.7, 135.7, 127.2, 120.5, 118.6,
3-Ethyl-1-phenyl-1H-indole (23): Light yellow oil; yield:
126 mg (57%); Rf 0.53 (hexane); IR (neat): n=3051, 2963,
8
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