4-Fluorobenzyl bromide → {3-[2-(4-Fluoro-benzyl)-1,1-dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl]-5-methyl-indol-1-yl}-acetic acid

HRID 1013201Notes

Reaction equation

C([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([CH:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[S:20](=[O:28])(=[O:27])[NH:19]2)=[CH:9]1)(C)(C)C.[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>>[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][N:19]2[CH:18]([C:10]3[C:11]4[C:16](=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=4)[N:8]([CH2:7][C:6]([OH:5])=[O:29])[CH:9]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[S:20]2(=[O:27])=[O:28])=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 680214-Fluorobenzyl bromide

HCID 67317704[3-(1,1-Dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-5-methyl-indol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 59753816{3-[2-(4-Fluoro-benzyl)-1,1-dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl]-5-methyl-indol-1-yl}-acetic acid

Procedure

The title compound was prepared by the method described for example 14 using the product from example 2, step c) and 4-fluorobenzyl bromide. 1H NMR (DMSO-d6) 8.00 (d, J=6.6 Hz, 1H), 7.66-7.58 (m, 2H), 7.39 (s, 1H), 7.24 (dd, J=3.0, 8.4 Hz, 2H), 7.22-7.20 (m, 1H), 7.04 (t, J=8.8 Hz, 2H), 6.90 (d, J=8.1 Hz, 1H), 6.76 (s, 1H), 5.75 (s, 1H), 4.94 (s, 2H), 4.50 (d, J=15.9 Hz, 1H), 3.97 (d, J=15.9 Hz, 1H), 2.16 (s, 3H); MS: ESI (negative): 463 (M−H).

Sources & evidence

ORD record: ord-d68d557e39b94996a4a8859266a71fe4
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981912B2

Reaction notes

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