Phenethyl bromide → [3-(1,1-Dioxo-2-phenethyl-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-5-methoxy-indol-1-yl]-acetic acid

HRID 1013207

Reaction equation

C([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[S:21](=[O:29])(=[O:28])[NH:20]2)=[CH:9]1)(C)(C)C.Br[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[O:28]=[S:21]1(=[O:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH:19]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:8]([CH2:7][C:6]([OH:5])=[O:30])[CH:9]=2)[N:20]1[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Reactant 2

HCID 7666Phenethyl bromide

HCID 67316901[3-(1,1-Dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-5-methoxy-indol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 59753843[3-(1,1-Dioxo-2-phenethyl-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-5-methoxy-indol-1-yl]-acetic acid

Procedure

The title compound was prepared by the method described for example 14 using the product from example 4, step c) and 2-bromoethylbenzene. 1H NMR (DMSO-d6) 13.03 (bs, 1H), 7.98 (d, J=8.7 Hz, 1H), 7.65-7.60 (m, 2H), 7.50 (s, 1H), 7.29 (d, J=9.0 Hz, 1H), 7.25-7.13 (m, 4H), 7.09 (d, J=8.1 Hz, 2H), 6.74 (dd, J=2.4, 9.0 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 5.95 (s, 1H), 5.00 (s, 2H), 3.51 (s, 3H), 3.42 (ddd, J=6.3, 10.2, 15.9 Hz, 1H), 3.14 (ddd, J=5.7, 9.9, 15.0 Hz, 1H), 3.00-2.70 (m, 2H); MS: ESI (negative): 475 (M−H).

Sources & evidence

ORD record: ord-f9b3487ef5e34ca3938e4630fb3e9761
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981912B2

Linked notes

Loading…