Allyl bromide → [3-(2-Allyl-1,1-dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-5-chloro-2-methyl-indol-1-yl]-acetic acid

HRID 750670Notes

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

Participants

Reactant 2

HCID 7841Allyl bromide

HCID 67316509HCID 67316509, compound

Product 1

HCID 59753818[3-(2-Allyl-1,1-dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-5-chloro-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 allyl bromide. 1H NMR (DMSO-d6) 13.14 (bs, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.67-7.59 (m, 2H), 7.45 (d, J=8.7 Hz, 1H), 7.06 (d, J=6.3 Hz, 1H), 7.02 (dd, J=1.8, 8.7 Hz, 1H), 6.83 (s, 1H), 5.96 (s, 1H), 5.82-5.69 (m, 1H), 5.14 (d, J=7.5 Hz, 1H), 5.10 (s, 1H), 5.03 (s, 2H), 3.90 (dd, J=4.8, 15.9 Hz, 1H), 3.45-3.36 (m, 1H), 2.37 (s, 3H); MS: ESI (negative): 429, 431 (M−H).

Sources & evidence

ORD record: ord-c9b10f0f150b4e7da5745cda554d9564
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405215B2

Reaction notes

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