4-Nitrobenzyl bromide → 1h-Indole-2-carboxylic acid,1-[(4-nitrophenyl)methyl]-3-(2-thienyl)-,ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)([O-:22])=[O:21]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:27][C:26]2[CH:29]=[CH:30][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=2)[C:8]2[C:13]([C:14]=1[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]Participants
3
Procedure
1-(4-Nitro-benzyl)-3-thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester was prepared from 3-thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester and 4-nitrobenzyl bromide followed the procedure of Example 3 Step 1 as a yellow powder: 1H NMR (DMSO-d6) δ 1.02 (t, J=7.2 Hz, 3H), 4.15 (q, J=7.2 Hz, 2H), 7.20 (dd, J=6.9, 3.4 Hz, 1H), 7.24 (dd, J=6.2, 0.8 Hz, 1H), 7.25-7.27 (m, 1H), 7.31 (d, J=8.8 Hz, 2H), 7.37-7.43 (m, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.68 (dd, J=5.2, 1.2 Hz, 1H), 7.71 (d, J=4.1 Hz, 1H), 8.19 (d, J=8.8 Hz, 2H); MS (ESI) m/z 407 (MH+); 405 ([M−H]−); Anal. calcd for C22H18N2O4S: C, 65.01; H, 4.46; N, 6.89 Found: C, 65.04; H, 6.62; N, 6.82.
Sources & evidence
- ORD record
- ord-9455edfd75604ee0b3d68ad931cdd68c
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07268159B2
Reaction notes
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