Phenylboronic Acid → 1h-Indole-2-carboxylic acid,1-[[4-(phenylamino)phenyl]methyl]-3-(2-thienyl)-

HRID 916201Notes

Reaction equation

C([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])C.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[NH:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[C:6]2[C:4]([OH:3])=[O:5])=[CH:26][CH:25]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 694339351h-Indole-2-carboxylic acid,1-[(4-aminophenyl)methyl]-3-(2-thienyl)-,ethyl ester

Product 1

HCID 114644131h-Indole-2-carboxylic acid,1-[[4-(phenylamino)phenyl]methyl]-3-(2-thienyl)-

Procedure

The title compound was prepared from 1-(4-amino-benzyl)-3-thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester and phenylboronic acid followed the procedure of Example 16 as a light green solid: 1H NMR (DMSO-d6) δ 5.70 (s, 2H), 6.78 (td, J=7.4, 1.0 Hz, 1H), 6.98 (d, J=8.7 Hz, 2H), 7.01 (dd, J=8.5, 1.0 Hz, 2H), 7.04 (d, J=8.7 Hz, 2H), 7.16 (t, J=3.5 Hz, 1H), 7.17 (dd, J=5.2, 1.6 Hz, 2H), 7.21 (dd, J=6.9, 2.1 Hz, 2H), 7.33-7.37 (m, 1H), 7.61 (dd, J=5.1, 1.3 Hz, 1H), 7.66 (t, J=8.7 Hz, 2H), 8.12 (br s, 1H), 13.34 (br s, 1H); MS (ESI) m/z 425 (MH+); MS (ESI) m/z 423 ([M−H]−); HRMS calcd for C26H21N2O2S: 425.1321; found (ESI+): 425.1319.

Sources & evidence

ORD record: ord-441181acc4a241c68836f17679007112
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268159B2

Reaction notes

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