5-Bromo-2-oxindole → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879462Notes

Reaction equation

HRID 879462 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:29]([CH3:30])=[CH:28][C:13]2[N:14]=[C:15]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22](C)[C:21](=[O:27])[CH2:20]4)[S:16][C:12]=2[C:11]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].BrC1C=C2C(=CC=1)NC(=O)C2>>[C:1]([O:5][C@@H:6]([C:10]1[C:29]([CH3:30])=[CH:28][C:13]2[N:14]=[C:15]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:27])[CH2:20]4)[S:16][C:12]=2[C:11]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 6111935-Bromo-2-oxindoleHCID 86700274(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid

Product 1

HCID 86700273(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid

Procedure

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid was prepared in a similar manner as (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid except 5-bromoindolin-2-one was used instead of 5-bromo-1-methylindolin-2-one. LCMS-ESI+: calc'd C28H26ClN2O4S: 521.1 (M+H+); Found: 521.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ: 7.91-7.88 (m, 2 H), 7.77 (s, 1H), 7.66 (m, 1H), 7.59-7.56 (m, 2H), 6.99 (d, 1H), 5.23 (s, 1H), 3.61 (s, 2H), 2.63 (s, 3H), 2.59 (s, 3H), 0.96 (s, 9H).

Sources & evidence

ORD record
ord-ae50871ef3014f3ab99dec1969b75564
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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