3-Bromo-5-fluorobenzoic acid → 3'-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)-5-fluorobiphenyl-3-carboxylic acid
Reaction equation
[CH:1]1([N:6]2[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=4)=[CH:15][C:8]=3[S:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([F:37])[CH:36]=1)[C:31]([OH:33])=[O:32]>>[CH:1]1([N:6]2[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:19]=[C:20]([C:28]5[CH:36]=[C:35]([F:37])[CH:34]=[C:30]([C:31]([OH:33])=[O:32])[CH:29]=5)[CH:21]=[CH:22][CH:23]=4)=[CH:15][C:8]=3[S:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
3
Procedure
A mixture of 3-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)phenylboronic acid (0.050 g, 0.14 mmol), 3-bromo-5-fluorobenzoic acid (0.044 g, 0.20 mmol) were coupled according to the general procedure to afford the title product. The crude residue was purified using automated prep-HPLC to yield the desired compound as pale yellow solid (0.010 g, over two steps 15%). 1H NMR (400 MHz, CDCl3): δ 8.11 (s, 1H), 7.91-7.66 (m, 4H), 7.50-7.24 (m, 4H), 7.03 (s, 1H), 5.24 (s, 2H), 4.64-4.60 (m, 1H), 2.18-2.15 (m, 2H), 1.88-1.66 (m, 6H). LC-MS (ESI) Calcd for C26H22FNO4S [M+H]+: 463.12. Found: 464.00.
Sources & evidence
- ORD record
- ord-f8bdcacaf1d64263b9ad8503aaa9a239
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748632B2
Reaction notes
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