Job/Unit: O30744
/KAP1
Date: 15-08-13 11:00:21
Pages: 12
A. E. Putra, K. Takigawa, H. Tanaka, Y. Ito, Y. Oe, T. Ohta
FULL PAPER
3-Decyl-1H-indole (5b):[19] Yellow oil. 1H NMR (CDCl3): δ = 0.86–
1.47 [m, 17 H, -(CH2)7-CH3], 1.70 [quintet, J = 7.8 Hz, 2 H, -CH2-
(CH2)7-CH3], 2.74 [t, J = 7.8 Hz, 2 H, -CH2-(CH2)8-CH3], 6.95 (s,
1 H, -NH-CH=), 7.09 (t, J = 7.5 Hz, 1 H, Ar), 7.16 (t, J = 7.5 Hz,
1 H, Ar), 7.33 (d, J = 7.5 Hz, 1 H, Ar), 7.60 (d, J = 7.5 Hz, 1 H,
Ar), 8.00 (br., 1 H, -NH-) ppm. 13C NMR (CDCl3): δ = 14.1, 22.7,
25.1, 29.3, 29.5, 29.7 (ϫ3), 30.1, 31.9, 110.8, 117.0, 118.8 (ϫ2),
120.8, 121.6, 127.4, 136.1 ppm. GC–MS: m/z = 257. HRMS (FAB,
m-NBA): calcd. for C18H27N 257.2144; found 257.2125.
Acknowledgments
A. E. P. gratefully thanks the Yoshida Scholarship Foundation for
awarding a doctoral scholarship.
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3-(1-Phenylethyl)-1H-indole (5c):[19] White solid; m.p. 70–71 °C. 1H
NMR (CDCl3): δ = 1.63 (d, J = 7.0 Hz, 3 H, -CH-CH3), 4.31 (q,
J = 7.0 Hz, 1 H, -CH-CH3), 6.95–7.05 (m, 2 H, Ar), 7.10–7.36 (m,
8 H, Ar), 10.86 (br., 1 H, -NH-) ppm. 13C NMR (CDCl3): δ = 22.4,
36.9, 110.8, 119.0, 119.5, 120.9, 121.3, 121.8, 125.7, 126.7, 127.2,
128.1, 136.4, 146.6 ppm. GC–MS: m/z = 221. HRMS (FAB, m-
NBA): calcd. for C16H15N 221.1205; found 221.1214.
3-(Diphenylmethyl)-1H-indole (5d):[20] White solid; m.p. 125–
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126 °C. H NMR (CDCl3): δ = 5.66 [s, 1 H, -CH(Ph)2], 6.53 (s, 1
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H, Ar), 7.01 (t, J = 7.0 Hz, 1 H, Ar), 7.10–7.35 (m, 13 H, Ar), 7.91
(br., 1 H, -NH-) ppm. 13C NMR (CDCl3): δ = 48.7, 110.9, 119.2,
119.7, 121.9, 123.8, 126.0, 126.8, 128.1, 128.3, 128.8, 136.4,
143.7 ppm. GC–MS: m/z = 283. HRMS (FAB, m-NBA): calcd. for
C21H17N 283.1361; found 283.1363.
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3-Cyclohexyl-1H-indole (5e):[21] Brown solid; m.p. 72–77 °C. 1H
NMR (CDCl3): δ = 1.18–2.12 [m, 10 H, -(CH2)5-], 2.93 (br., 1 H,
CH-), 6.92 (s, 1 H, -NH-CH=), 7.08 (t, J = 7.5 Hz, 1 H, Ar), 7.16
(t, J = 7.5 Hz, 1 H, Ar), 7.33 (d, J = 7.5 Hz, 1 H, Ar), 7.65 (d, J
= 7.5 Hz, 1 H, Ar), 7.91 (br., 1 H, -NH-) ppm. 13C NMR (CDCl3):
δ = 26.5, 26.9, 34.0, 35.4, 110.9, 118.7, 119.1 (ϫ2), 121.6, 123.0,
126.6, 136.2 ppm. GC–MS: m/z = 199. HRMS (FAB, m-NBA):
calcd. for C14H17N 199.1361; found 199.1362.
3-(Pyridin-2-ylmethyl)-1H-indole (5f):[22] White solid; m.p. 89–
1
90 °C. H NMR (CDCl3): δ = 4.31 (s, 2 H, -CH2-), 7.04–7.20 (m,
6 H, Ar), 7.35 (d, J = 8.1 Hz, 1 H, Ar), 7.51 (d, J = 7.8 Hz, 1 H,
Ar), 8.08 (br., 1 H, -NH-), 8.55 (d, J = 3.9 Hz, 1 H, Ar) ppm. 13C
NMR (CDCl3): δ = 34.5, 111.0, 113.4, 118.9, 119.1, 120.9, 121.7
(ϫ2), 122.6, 126.2, 136.3, 148.7, 161.0 ppm. GC–MS: m/z = 208.
HRMS (FAB, m-NBA): calcd. for C14H12N2 208.1000; found
208.1004.
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3-(Cyclohexylmethyl)-1H-indole (5g): White solid; m.p. 64–66 °C.
1H NMR (CDCl3): δ = 0.94–1.03 (m, 2 H, -Cy), 1.15–122 (m, 2
H, -Cy), 1.56–1.73 (m, 6 H, -Cy), 2.63 (d, J = 6.9 Hz, 2 H, CH-
CH2-), 6.93 (s, 1 H, -NH-CH=), 7.07–7.19 (m, 2 H, Ar), 7.35 (d, J
= 1.8 Hz, 1 H, Ar), 7.61 (d, J = 7.8 Hz, 1 H), 7.85 (s, 1 H, -NH-)
ppm. 13C NMR (CDCl3): δ = 26.3, 26.5, 33.0, 33.5, 38.7, 110.8,
115.4, 118.9, 119.1, 121.6, 121.8, 127.9, 136.1 ppm. GC–MS: m/z
= 213.
3-(1-Methylheptyl)-1H-indole (5h):[5b] Pale yellow oil. 1H NMR
(CDCl3): δ = 0.83–0.90 (m, 3 H, -CH2-CH3), 1.25–131 (m, 8 H,
-C4H8-CH3), 1.35 (d, J = 6.9 Hz, 3 H, CH-CH3), 1.58–1.62 (m, 1
H), 1.75–1.80 (m, 1 H), 3.05 (m, 1 H, CH3-CH), 6.94 (s, 1 H, -NH-
CH=), 7.06–7.19 (m, 2 H, Ar), 7.36 (d, J = 6.9 Hz, 1 H, Ar), 7.66
(d, J = 3.8 Hz, 1 H), 7.86 (s, 1 H, -NH-) ppm. 13C NMR (CDCl3):
δ = 14.1, 21.3, 22.6, 27.6, 29.5, 30.80, 31.87, 37.65, 111.0, 118.9,
119.4, 119.7, 121.7, 122.9, 126.9, 136.4 ppm. HRMS (FAB, m-
NBA): calcd. for C16H23N 229.1830; found 229.1850.
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Supporting Information (see footnote on the first page of this arti-
cle): 1H and 13C NMR spectra of compounds 3a–3r, 4a–4e, and
5a–5h.
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