Methanesulfonyl chloride → 1h-Indole-2-carboxylic acid,1-[[4-[(methylsulfonyl)amino]phenyl]methyl]-3-(2-thienyl)-

HRID 916198Notes

Reaction equation

HRID 916198 reaction equation
C([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])C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>>[CH3:30][S:31]([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)(=[O:33])=[O:32]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 694355411h-Indole-2-carboxylic acid,1-[(4-nitrophenyl)methyl]-3-(2-thienyl)-,ethyl ester

Product 1

HCID 114188941h-Indole-2-carboxylic acid,1-[[4-[(methylsulfonyl)amino]phenyl]methyl]-3-(2-thienyl)-

Procedure

The title compound was prepared from 1-(4-nitro-benzyl)-3-thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester and methanesulfonyl chloride followed the procedure of Example 3 Step 2 as a light yellow solid: 1H NMR (DMSO-d6) δ 2.94 (s, 3H), 5.76 (s, 2H), 7.08-7.24 (m, 7H), 7.34 (td, J=8.4, 1.2 Hz, 1H), 7.60-7.70 (m, 3H), 9.69 (br s, 1H), 13.25 (br s, 1H); MS (ESI) m/z 427 (MH+); MS (ESI) m/z 425 ([M−H]−); HRMS calcd for C21H19N2O4S2: 427.0784; found (ESI+): 427.0779.

Sources & evidence

ORD record
ord-af0d50102870463eaf6ec5fea061781d
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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