Trifluoroacetic acid → 1h-Indole-2-carboxylic acid,1-[(4-aminophenyl)methyl]-3-(2-thienyl)-,ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=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].C(O)(C(F)(F)F)=O>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=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-Amino-benzyl)-3-thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester was prepared from 1-(4-nitro-benzyl)-3-thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester followed the procedure of Example 1 Step 1: 1H NMR (DMSO-d6) δ 1.10 (t, J=7.2 Hz, 3H), 4.20 (q, J=7.2 Hz, 2H), 5.01 (br s, 2H), 5.55 (s, 2H), 6.45 (d, J=8.5 Hz, 2H), 6.84 (d, J=8.5 Hz, 2H), 7.16-7.20 (m, 3H), 7.35 (td, J=7.3, 1.0 Hz, 1H), 7.62 (dd, J=5.2, 1.2 Hz, 1H), 7.65 (d, J=4.1 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H); MS (ESI) m/z 377 (MH+); 375 ([M−H]−); Anal. calcd for C22H20N2O2S.0.05 TFA C, 69.46; H, 5.29; N, 7.33. Found: C, 69.66; H, 5.04; N, 7.72.
Sources & evidence
- ORD record
- ord-43b55ecd030747f4adc1a6577c7a9d7e
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07268159B2
Reaction notes
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