The Journal of Organic Chemistry
Page 6 of 13
2920, 2849, 1560, 1533, 1510, 1465, 1454, 1343, 1318, 1107, 866,
methylindole and 2-bromonaphthalene as reactants. The
product was isolated by column chromatography (PE:EA =
+
1
2
3
4
5
6
7
8
854, 791, 750, 704, 696. HRMS (APCI) calcd for C15H13N2O2
[(M+H)+]: 253.0972; found: 253.0980.
100:1) as a light yellow solid (23.2 mg, 30 %) Spectral data is
consistent with previous reports.25 1H NMR (400 MHz,
CDCl3) δ 8.03 – 7.90 (m, 4H), 7.69 (dd, J = 15.3, 8.1 Hz, 2H),
7.60 – 7.53 (m, 2H), 7.43 (d, J = 8.2 Hz, 1H), 7.32 (t, J = 7.4 Hz,
1H), 7.21 (t, J = 7.3 Hz, 1H), 6.71 (s, 1H), 3.84 (s, 3H). 13C NMR
(101 MHz, CDCl3) δ 141.7, 138.6, 133.4, 132.8, 130.3, 128.4, 128.3,
128.2, 128.2, 127.9, 127.3, 126.7, 126.5, 121.9, 120.6, 120.1, 109.8,
102.2, 31.5. HRMS (APCI) calcd for C19H16N+ [(M+H)+]:
258.1277; found: 258.1279.
2-([1,1'-biphenyl]-4-yl)-1-methylindole (3t). The compound
was prepared following the general procedure using 1-
methylindole and 4-bromo-1,1'-biphenyl as reactants. The
product was isolated by column chromatography (PE:EA =
100:1) as a light yellow solid (45.1 mg, 53 %) Spectral data is
consistent with previous reports.26 1H NMR (400 MHz,
CDCl3) δ 7.71 – 7.67 (m, 2H), 7.65 (dd, J = 5.2, 3.3 Hz, 3H), 7.61
– 7.55 (m, 2H), 7.47 (dd, J = 10.4, 4.8 Hz, 2H), 7.41 – 7.34 (m,
2H), 7.29 – 7.23 (m, 1H), 7.19 – 7.11 (m, 1H), 6.61 (s, 1H), 3.78
(s, 3H) 13C NMR (101 MHz, CDCl3) δ 141.3, 140.8, 140.6, 138.6,
131.8, 129.8, 129.0, 128.1, 127.7, 127.3, 127.2, 121.9, 120.6, 120.0,
109.8, 101.9, 31.4. HRMS (APCI) calcd for C21H18N+ [(M+H)+]:
284.1434; found: 284.1438.
1-methyl-2-(4-(trifluoromethyl)phenyl)-indole (3o). The
compound was prepared following the general procedure
using
1-methylindole
and
1-bromo-4-
(trifluoromethyl)benzene as reactants. The product was iso-
lated by column chromatography (PE:EA = 20:1) as a light
yellow solid (51.2 mg, 62 %). Spectral data is consistent with
previous reports.18 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J =
8.1 Hz, 2H), 7.65 (t, J = 8.7 Hz, 3H), 7.40 (d, J = 8.2 Hz, 1H),
7.33 – 7.27 (m, 1H), 7.22 – 7.15 (m, 1H), 6.64 (s, 1H), 3.78 (s,
3H) 13C NMR (101 MHz, CDCl3) δ 139.7, 138.7, 136.4, 129.8 (q,
J = 32.5 Hz), 129.4, 127.8, 125.5 (q, J = 3.7 Hz), 122.4, 121.8 (q, J =
205.8 Hz), 120.8, 120.2, 109.8, 102.8, 31.3. 19F NMR (376 MHz,
CDCl3) δ -62.51 (s). HRMS (APCI) calcd for C16H13F3N+
[(M+H)+]: 276.0995; found: 276.1000.
4-(1-methylindol-2-yl)benzaldehyde (3p). The compound
was prepared following the general procedure using 1-
methylindole and 4-bromobenzaldehyde as reactants. The
product was isolated by column chromatography (PE:EA =
20:1) as a light yellow solid (33.2 mg, 47 %). Spectral data is
consistent with previous reports.24 1H NMR (400 MHz,
CDCl3) δ 10.08 (s, 1H), 8.08 – 7.91 (m, 2H), 7.73 – 7.61 (m, 3H),
7.40 (dd, J = 8.2, 0.5 Hz, 1H), 7.31 (ddd, J = 8.2, 7.1, 1.1 Hz, 1H),
7.22 – 7.13 (m, 1H), 6.70 (d, J = 0.5 Hz, 1H), 3.80 (s, 3H) 13C
NMR (101 MHz, CDCl3) δ 190.9, 139.1, 138.2, 137.9, 134.4, 129.1,
128.6, 126.9, 121.7, 120.0, 119.4, 109.0, 102.6, 30.7. IR (neat/cm-
1) 3052, 2922, 2852, 2735, 1702, 1604, 1567, 1466, 1389, 1359,
1341, 1318, 1305, 1207, 1168, 843, 786, 750. HRMS (APCI) calcd
for C16H14NO+ [(M+H)+]: 236.1070; found: 236.1074.
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1-(3-(1-methylindol-2-yl)phenyl)ethan-1-one (3u). The
compound was prepared following the general procedure
using 1-methylindole and 1-(3-bromophenyl)ethan-1-one as
reactants. The product was isolated by column chromatog-
1
raphy (PE:EA = 40:1) as a light yellow oil (41.1 mg, 55 %) H
NMR (400 MHz, CDCl3) δ 8.11 (t, J = 1.6 Hz, 1H), 8.03 – 7.94
(m, 1H), 7.75 – 7.69 (m, 1H), 7.65 (d, J = 7.9 Hz, 1H), 7.58 (t, J
= 7.7 Hz, 1H), 7.38 (d, J = 8.2 Hz, 1H), 7.31 – 7.25 (m, 1H), 7.20
– 7.12 (m, 1H), 6.62 (s, 1H), 3.76 (s, 3H), 2.66 (s, 3H). 13C NMR
(101 MHz, CDCl3) δ 198.0, 140.4, 138.6, 137.5, 133.9, 133.5,
129.2, 129.0, 128.0, 127.8, 122.2, 120.8, 120.2, 109.8, 102.4, 31.4,
26.9. IR (neat/cm-1) 3055, 2923, 2852, 1686, 1602, 1580, 1538,
1464, 1418, 1385, 1356, 1341, 1315, 1279, 1266, 1237, 1201, 783, 750,
736, 696, 589. HRMS (APCI) calcd for C17H16NO+ [(M+H)+]:
250.1226; found: 250.1230.
N-(2-methyl-4-(1-methylindol-2-yl)phenyl)acetamide
(3q). The compound was prepared following the general
procedure using 1-methylindole and N-(4-bromo-2-
methylphenyl)acetamide as reactants. The product was iso-
lated by column chromatography (PE:EA = 2:1) as a light yel-
1
low solid (54.3 mg, 65 %). M. P. 162.0-163.5 oC H NMR (400
MHz, CDCl3) δ 7.92 – 7.83 (m, 1H), 7.61 (d, J = 7.8 Hz, 1H),
7.37 – 7.30 (m, 3H), 7.27 – 7.21 (m, 1H), 7.13 (t, J = 7.4 Hz, 2H),
6.51 (s, 1H), 3.72 (s, 3H), 2.31 (s, 3H), 2.23 (s, 3H) 13C NMR (101
MHz, CDCl3) δ 168.6, 141.2, 138.4, 135.5, 131.5, 129.8, 129.4,
128.0, 127.8, 123.4, 121.7, 120.5, 119.9, 109.7, 101.6, 31.3, 24.5, 18.0.
IR (neat/cm-1) 3274, 3050, 2922, 1666, 1612, 1587, 1518, 1465,
1433, 1369, 1339, 1301, 1266, 1242, 1009, 837, 784, 751, 736, 702.
HRMS (APCI) calcd for C18H19N2O+ [(M+H)+]: 279.1492;
found: 279.1496.
6-methoxy-2-(4-methoxyphenyl)-1-methylindole
(3v).
The compound was prepared following the general proce-
dure using 6-methoxy-1-methylindole and 1-bromo-4-
methoxybenzene as reactants. The product was isolated by
column chromatography (PE:EA = 50:1) as a light yellow
solid (48.9 mg, 61 %) Spectral data is consistent with previ-
ous reports.27 1H NMR (400 MHz, CDCl3) δ 7.53 – 7.48 (m,
1H), 7.45 – 7.41 (m, 2H), 7.03 – 6.99 (m, 2H), 6.85 – 6.82 (m,
2H), 6.44 (s, 1H), 3.92 (s, 3H), 3.88 (s, 3H), 3.69 (s, 3H). 13C
NMR (101 MHz, CDCl3) δ 159.4, 156.3, 140.6, 139.0, 130.6,
125.6, 122.4, 121.0, 114.1, 109.6, 100.9, 93.5, 55.9, 55.5, 31.3.
ethyl 2-(4-(1-methylindol-2-yl)phenyl)acetate (3r). The
compound was prepared following the general procedure
using 1-methylindole and ethyl 2-(4-bromophenyl)acetate as
reactants. The product was isolated by column chromatog-
raphy (PE:EA = 10:1) as a light yellow solid (47.5 mg, 54 %) M.
5-fluoro-2-(4-methoxyphenyl)-1-methylindole (3w). The
compound was prepared following the general procedure
1
P. 64.3-66.2 oC. H NMR (400 MHz, CDCl3) δ 7.62 (d, J = 7.8
Hz, 1H), 7.46 (d, J = 7.8 Hz, 2H), 7.41 – 7.31 (m, 3H), 7.23 (dd, J
= 14.2, 6.1 Hz, 1H), 7.13 (t, J = 7.4 Hz, 1H), 6.55 (s, 1H), 4.18 (q, J
= 7.1 Hz, 2H), 3.72 (s, 3H), 3.66 (s, 2H), 1.28 (t, J = 7.1 Hz, 3H)
13C NMR (101 MHz, CDCl3) δ 171.5, 141.3, 138.5, 134.0, 131.7,
129.6, 129.5, 128.1, 121.8, 120.6, 120.0, 109.7, 101.8, 61.1, 41.2, 31.3,
14.3. IR (neat/cm-1) 3053, 2979, 2936, 1734, 1611, 1502, 1465,
1431, 1415, 1385, 1367, 1339, 1315, 1251, 1223, 1157, 1031, 826, 781,
using
5-fluoro-1-methylindole
and
1-bromo-4-
methoxybenzene as reactants. The product was isolated by
column chromatography (PE:EA = 50:1) as a light yellow
o
1
solid (47.5 mg, 62 %) M. P. 107.2-108.9 C. H NMR (400
MHz, CDCl3) δ 7.54 (dd, J = 8.5, 5.4 Hz, 1H), 7.43 (d, J = 8.5
Hz, 2H), 7.04 (dd, J = 12.0, 4.8 Hz, 3H), 6.92 (t, J = 9.2 Hz,
1H), 6.49 (s, 1H), 3.89 (s, 3H), 3.68 (s, 3H). 13C NMR (101
MHz, CDCl3) δ 159.8 (d, J = 237.1 Hz), 159.6, 142.1 (d, J = 3.8
Hz), 138.3 (d, J = 12.0 Hz), 130.6, 125.1, 124.5, 121.0 (d, J = 10.0
Hz), 114.1, 108.4 (d, J = 24.4 Hz), 101.1, 96.1 (d, J = 26.2 Hz),
55.5, 31.3. 19F NMR (376 MHz, CDCl3) δ -120.94 (s). IR
+
750, 736. HRMS (APCI) calcd for C19H20NO2 [(M+H)+]:
294.1489; found: 294.1490.
1-methyl-2-(naphthalen-2-yl)indole (3s). The compound
was prepared following the general procedure using 1-
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