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

HRID 750672Notes

Reaction equation

C([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl: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)=[C:9]1[CH3:29])(C)(C)C.[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1>>[Cl:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][C:6]([OH:5])=[O:30])[C:9]([CH3:29])=[C:10]2[CH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[S:20](=[O:28])(=[O:27])[N:19]1[CH2:36][C:35]1[CH:38]=[CH:39][C:32]([F:31])=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 680214-Fluorobenzyl bromide

HCID 67316509HCID 67316509, compound

Product 1

HCID 59753812{5-Chloro-3-[2-(4-fluoro-benzyl)-1,1-dioxo-2,3-dihydro-1h-1lambda6-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 6, step c) and 4-fluorobenzyl bromide. 1H NMR (DMSO-d6) 13.2 (bs, 1H), 8.05 (d, J=8.1 Hz, 1H), 7.67 (t, J=7.2 Hz, 1H), 7.62 (dt, J=1.5, 7.5 Hz, 1H), 7.44 (d, J=8.6 Hz, 1H), 7.19-6.96 (m, 6H), 6.83 (s, 1H), 5.83 (s, 1H), 5.01 (d, J=18.3 Hz, 1H), 5.00 (d, J=18.3 Hz, 1H), 4.50 (d, J=15.6 Hz, 1H), 3.83 (d, J=15.6 Hz, 1H), 2.11 (s, 3H); MS: ESI (negative): 497, 499 (M−H).

Sources & evidence

ORD record: ord-5edfaa342ea04a3b8b6014a235beae77
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405215B2

Reaction notes

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