2-Bromoethanol → rac-{3-[2-(2-Hydroxy-ethyl)-1,1-dioxo-2,3-dihydro-1H-1lambda6-benzo[d]isothiazol-3-yl]-2-methyl-indol-1-yl}-acetic acid

HRID 750650Notes

Reaction equation

C([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19](=[O:27])(=[O:26])[NH:18]2)=[C:9]1[CH3:28])(C)(C)C.Br[CH2:31][CH2:32][OH:33]>>[OH:33][CH2:32][CH2:31][N:18]1[CH:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][C:6]([OH:29])=[O:5])[C:9]=2[CH3:28])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:19]1(=[O:27])=[O:26]

Participants

Reactant 2

HCID 108982-Bromoethanol

HCID 67317115[3-(1,1-Dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-2-methyl-indol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 46890209rac-{3-[2-(2-Hydroxy-ethyl)-1,1-dioxo-2,3-dihydro-1H-1lambda*6*-benzo[d]isothiazol-3-yl]-2-methyl-indol-1-yl}-acetic acid

Procedure

The title compound was prepared by the method described for example 14 using the product from example 3, step c) and 2-bromoethanol. 1H NMR (DMSO-d6) δ 7.98-7.95 (m, 1H), 7.62-7.58 (m, 3H), 7.36 (d, J=8.4 Hz, 1H), 7.04-7.01 (m, 2H), 6.80-6.78 (m, 1H), 6.14 (s, 1H), 5.00 (s, 2H), 4.75 (bs, 1H), 3.59-3.53 (m, 1H), 3.26-3.17 (m, 2H), 3.02-2.92 (m, 1H), 2.39 (s, 3H); MS: ESI (negative): 399 (M−H).

Sources & evidence

ORD record: ord-82d2d22199e64879a9cf1dc112951112
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405215B2

Reaction notes

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