Trifluoroacetic acid → 1-(4-Amino-benzyl)-3-phenyl-1H-indole indolecarboxylic acid ethyl ester

HRID 916191Notes

Reaction equation

HRID 916191 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[NH2:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:6]2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 694373881h-Indole-2-carboxylic acid,1-[(4-nitrophenyl)methyl]-3-phenyl-,ethyl ester

Product 1

HCID 694354711-(4-Amino-benzyl)-3-phenyl-1H-indole indolecarboxylic acid ethyl ester

Procedure

1-(4-Amino-benzyl)-3-phenyl-1H-indole indolecarboxylic acid ethyl ester was prepared from 1-(4-nitro-benzyl)-3-phenyl-1H-indolecarboxylic acid ethyl ester followed the procedure of Example 1 Step 1 as a yellow syrup: 1H NMR (DMSO-d6) δ 0.98 (t, J=7.2 Hz, 3H), 4.11 (q, J=7.2 Hz, 2H), 4.99 (br s, 2H), 5.59 (s, 2H), 6.44 (d, J=8.41 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 7.13 (td, J=7.1, 0.8 Hz, 1H), 7.34 (td, J=7.1, 0.8 Hz, 1H), 7.38-7.41 (m, 3H), 7.44-7.49 (m, 3H), 7.69 (d, J=8.4 Hz, 1H); MS (ESI) Hz 371 (MH+); 369 ([M−H]−); Anal. calcd for C24H22N2O2.0.04 TFA C, 71.12; H, 5.92; N, 7.47. Found: C, 71.03; H, 5.87; N, 7.36.

Sources & evidence

ORD record
ord-e383b6d1cc0345e580303ea8208c5f3d
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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