5
42
Chem. Pharm. Bull.
Vol. 63, No. 7 (2015)
13
4
.14 (s, 2H, CH Ph), 3.83 (s, 3H, NCH ); C-NMR (100MHz,
2,2,2-Trichloro-1-(1H-indol-3-yl)ethan-1-one (3ba) Pale
2
3
CDCl ) δ: 192.6, 137.4, 135.9, 135.7, 129.3, 128.5, 126.6, 123.5, green prisms from ethyl acetate/hexane; mp 234–237°C; IR
3
−
1
1
1
22.8, 122.7, 116.2, 109.5, 46.9, 33.5; HR-MS (ESI) m/z: Calcd νmax (KBr) cm : 3251 (NH), 1639 (CO); H-NMR (400MHz,
+
for C H NNaO (M+Na ) 272.1051. Found 272.1066.
DMSO-d ) δ: 12.52 (brs, 1H, NH), 8.58 (d, 1H, J=3.2Hz,
(3ah) C -H), 8.19–8.15 (m, 1H, arom-H), 7.59–7.55 (m, 1H, arom-H),
17
15
6
1
-(1-Methyl-1H-indol-3yl)-3-phenylpropan-1-one
Colorless prisms from chloroform/hexane; mp 66–69°C; IR 7.32–7.28 (m, 2H, arom-H); C-NMR (100MHz, DMSO-d6)
νmax (KBr) cm : 1644 (CO); H-NMR (400MHz, CDCl ) δ: δ: 176.8, 136.7, 136.2, 127.2, 123.9, 123.2, 121.3, 113.0, 104.8,
.40–8.38 (m, 1H, C -H), 7.31–7.17 (m, 9H, arom-H), 3.79 96.6; HR-MS (ESI) m/z: Calcd for C H Cl NNaO (M+Na )
s, 3H, NCH ), 3.18–3.08 (m, 4H, CH CH Ph); C-NMR 283.9413. Found 283.9429.
2
13
−1
1
3
+
8
(
4
10
6
3
13
3
2
2
(
100MHz, CDCl ) δ: 194.4, 141.8, 137.4, 135.2, 128.49, 128.47,
2,2,2-Trichloro-1-(2-methyl-1H-indol-3-yl)ethan-1-
3
1
26.3, 126.0, 123.3, 122.6, 122.5, 116.4, 109.6, 41.6, 33.4, 30.8; one (3ea) Brown needles from chloroform/hexane; mp
+
−1
HR-MS (ESI) m/z: Calcd for C H NNaO (M+Na ) 286.1208. 166–168°C; IR ν (KBr) cm : 3307 (NH), 1633 (CO);
Found 286.1224.
-(1-Methyl-1H-indol-3-yl)ethan-1-one
brown needles from ethyl acetate/hexane; mp 104–106°C; 7.30–7.24 (m, 2H, arom-H), 2.80 (s, 3H, arom-CH3); C-NMR
IR νmax (KBr) cm : 1639 (CO); H-NMR (400MHz, CDCl ) (100MHz, CDCl ) δ: 178.4, 150.5, 134.4, 124.8, 123.9, 123.0,
18
17
max
1
H-NMR (400MHz, CDCl ) δ: 8.77 (brs, 1H, NH), 8.25
Pale (dd, 1H, J=7.2, 1.2Hz, C -H), 7.36–7.34 (m, 1H, arom-H),
3
11,19)
1
(3ai)
4
13
−1
1
3
3
δ: 8.38–8.36 (m, 1H, C -H), 7.70 (s, 1H, C -H), 7.33–7.29 122.2, 110.9, 106.7, 97.7, 17.1; HR-MS (ESI) m/z: Calcd for
4
2
+
(
m, 3H, arom-H), 3.84 (s, 3H, NCH ), 2.52 (s, 3H, COCH ); C H Cl NNaO (M+Na ) 297.9569. Found 297.9545.
C-NMR (100MHz, CDCl ) δ: 192.9, 137.4, 135.7, 126.2,
3
3
11
8
3
1
3
2,2,2-Trichloro-1-(1-methyl-2-phenyl-1H-indol-3-yl)-
3
1
23.3, 122.5, 116.9, 109.6, 33.5, 27.6; HR-MS (ESI) m/z: Calcd ethan-1-one (3fa) Yellowish brown prisms from chloroform/
+
−1
for C H NNaO (M+Na ) 196.0738. Found 196.0756.
hexane; mp 132–133°C; IR ν
(KBr) cm : 1675 (CO);
max
1
1
11
11,19)
1
(
1-Methyl-1H-indol-3-yl)(phenyl)methanone
(3aj)
H-NMR (400MHz, CDCl ) δ: 8.29–8.27 (m, 1H, C -H),
3
4
Brown needles from chloroform/hexane; mp 116–118°C; IR 7.52–7.48 (m, 3H, arom-H), 7.43–7.40 (m, 1H, arom-H),
−1
1
13
νmax (KBr) cm : 1619 (CO); H-NMR (400MHz, CDCl ) δ: 7.38–7.35 (m, 4H, arom-H), 3.56 (s, 3H, NCH3); C-NMR
3
8
.44–8.41 (m, 1H, C -H), 7.80 (dd, 2H, J=8.0, 1.6Hz, arom- (100MHz, CDCl ) δ: 179.0, 150.8, 137.0, 131.6, 129.8, 129.3,
4
3
H), 7.54–7.52 (m, 2H, arom-H), 7.49–7.45 (m, 2H, arom-H), 128.6, 124.7, 123.7, 123.3, 122.4, 110.2, 107.5, 97.4, 31.2;
13
+
7
.36–7.34 (m, 3H, arom-H), 3.83 (s, 3H, NCH3); C-NMR HR-MS (ESI) m/z: Calcd for C H Cl NNaO (M+Na )
17 12 3
(100MHz, CDCl ) δ: 190.6, 140.7, 137.7, 137.3, 130.8, 128.4, 373.9882. Found 373.9854.
3
1
28.0, 127.0, 123.4, 122.56, 122.53, 115.4, 109.4, 33.3; HR-MS
2,2,2-Trichloro-1-(5-chloro-1H-indol-3-yl)ethan-1-one
+
(
2
ESI) m/z: Calcd for C H NNaO (M+Na ) 258.0895. Found (3ga) Brown prisms from ethyl acetate/hexane; mp
16
13
−1
58.0887.
238–243°C; IR ν
(KBr) cm : 3259 (NH), 1654 (CO);
max
1
(
4-Chlorophenyl)(1-methyl-1H-indol-3-yl)methanone
H-NMR (400MHz, DMSO-d ) δ: 12.69 (brs, 1H, NH), 8.65
6
11,19)
(3ak)
Pale brown prisms from ethyl acetate/hexane; (d, 1H, J=3.6Hz, C -H), 8.14 (d, 1H, J=2.0Hz, C -H), 7.59
2
4
−1
1
mp 149–150°C; IR νmax (KBr) cm : 1625 (CO); H-NMR (dd, 1H, J=8.8, 0.4Hz, C -H), 7.33 (dd, 1H, J=8.8, 2.4Hz,
7
13
(400MHz, CDCl ) δ: 8.39–8.37 (m, 1H, C -H), 7.73 (dd, 2H, C -H); C-NMR (100MHz, DMSO-d ) δ: 176.9, 138.0, 134.8,
3
4
6
6
J=8.4, 2.0Hz, C , C -H), 7.48 (s, 1H, C -H), 7.43 (dd, 2H, 128.4, 128.0, 124.0, 120.5, 114.7, 104.6, 96.2; HR-MS (ESI)
3
′
5′
2
+
J=8.4, 2.0Hz, C , C -H), 7.36–7.32 (m, 3H, arom-H), 3.82 m/z: Calcd for C H Cl NNaO (M+Na ) 317.9023. Found
2
3
′
6′
10
5
4
1
(
s, 3H, NCH3); C-NMR (100MHz, CDCl ) δ: 189.3, 139.2, 317.9014.
3
137.6, 137.5, 137.2, 130.0, 128.5, 127.0, 123.8, 122.8, 122.6,
Methyl-3-(2,2,2-trichloroacetyl)-1H-indole-5-carboxyl-
1
15.3, 109.7, 33.6; HR-MS (ESI) m/z: Calcd for C H ClNNaO ate (3ha) Orangish yellow needles from ethyl acetate/hex-
16
12
+
−1
(
M+Na ) 292.0505. Found 292.0500.
ane; mp 228–230°C; IR ν
(KBr) cm : 3243 (NH), 1687
max
1
(
1-Methyl-1H-indol-3-yl)(4-nitrophenyl)methanone (COO), 1666 (CO); H-NMR (400MHz, DMSO-d ) δ: 12.82
6
1
1,19)
(3al)
Yellowish black prisms from chloroform/hexane; (brs, 1H, NH), 8.86 (s, 1H, C -H), 8.79 (s, 1H, C -H), 7.91
4 2
−
1
mp 191–193°C; IR ν
(KBr) cm : 1616 (CO), 1517, 1344 (dd, 1H, J=8.8, 1.6Hz, arom-H), 7.66 (d, 1H, J=8.4Hz, arom-
max
1
13
(
NO2); H-NMR (400MHz, CDCl ) δ: 8.41–8.38 (m, 1H, H), 3.88 (s, 3H, COOCH3); C-NMR (100MHz, DMSO-d6)
3
C -H), 8.32 (dd, 2H, J=8.8, 2.0Hz, C , C -H), 7.92 (dd, δ: 177.1, 166.9, 139.0, 138.7, 126.9, 124.8, 124.5, 123.5, 113.3,
4
3′
5′
2
H, J=8.8, 2.0Hz, C , C -H), 7.49 (s, 1H, C -H), 7.40–7.37 105.7, 96.2, 52.2; HR-MS (ESI) m/z: Calcd for C H Cl NNaO
2′ 6′ 2 12 8 3 3
13
+
(m, 3H, arom-H), 3.87 (s, 3H, NCH3); C-NMR (100MHz, (M+Na ) 341.9467. Found 341.9485.
CDCl ) δ: 188.3, 149.0, 146.2, 138.0, 137.6, 129.3, 126.8, 124.1,
2,2,2-Trichloro-1-(5-nitro-1H-indol-3-yl)ethan-1-one
3
1
23.5, 123.2, 122.6, 115.2, 109.8, 33.7; HR-MS (ESI) m/z: (3ia) Yellowish colorless needles from ethyl acetate/hexane;
+
−1
Calcd for C H N NaO (M+Na ) 303.0746. Found 303.0739.
mp 253–254°C; IR ν
(KBr) cm : 3224 (NH), 1654 (CO),
1
6
12
2
3
max
19)
1
(
1-Methyl-1H-indol-3-yl)(p-tolyl)methanone
(3am)
1533, 1336 (NO ); H-NMR (400MHz, DMSO-d ) δ: 13.07
2
6
Pale yellow needles from chloroform/hexane; mp 143–144°C; (brs, 1H, NH), 9.02 (d, 1H, J=2.0Hz, C -H), 8.86 (d, 1H,
4
−
1
1
IR νmax (KBr) cm : 1617 (CO); H-NMR (400MHz, CDCl ) J=2.0Hz, C -H), 8.19 (dd, 1H, J=9.2, 2.0Hz, C -H), 7.77
δ: 8.43–8.39 (m, 1H, C -H), 7.74 (dd, 2H, J=6.4, 2.0Hz, (d, 1H, J=8.8Hz, C -H); C-NMR (100MHz, DMSO-d6)
arom-H), 7.54 (s, 1H, C -H), 7.39–7.31 (m, 3H, arom-H), 7.28 δ: 177.1, 143.7, 140.2, 139.6, 126.7, 119.3, 117.6, 114.0, 106.4,
3
2
6
13
4
7
2
+
(
d, 2H, J=8.0Hz, arom-H), 3.85 (s, 3H, NCH ), 2.44 (s, 3H, 95.9; HR-MS (ESI) m/z: Calcd for C H Cl N NaO (M+Na )
3
10
5
3
2
3
13
C H CH ); C-NMR (100MHz, CDCl ) δ: 190.6, 141.5, 140.3, 328.9263. Found 328.9274.
6
4
3
3
138.2, 137.5, 128.9, 128.8, 127.2, 123.5, 122.7, 122.5, 115.7,
2,2,2-Trichloro-1-(5-methoxy-1H-indol-3-yl)ethan-1-one
1
09.5, 33.5, 21.5; HR-MS (ESI) m/z: Calcd for C H NNaO (3ja) Green needles from chloroform/hexane; mp 198–201°C;
17
15
+
−1
1
(
M+Na ) 272.1051. Found 272.1027.
IR νmax (KBr) cm : 3255 (NH), 1641 (CO); H-NMR