3-Iodo-4-methoxybenzoic acid → 3'-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)-6-methoxybiphenyl-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.I[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[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:35]5[C:36]([O:37][CH3:38])=[CH:28][CH:29]=[C:30]([C:31]([OH:33])=[O:32])[CH:34]=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-iodo-4-methoxybenzoic acid (0.053 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 (0.013 g, over two steps 10%). 1H NMR (400 MHz, CDCl3): δ 7.80-7.66 (m, 2H), 7.60-7.34 (m, 5H), 7.23-7.21 (m, 2H), 6.79 (d, 1H, J=8.5 Hz), 5.02 (s, 2H), 4.44-4.30 (m, 1H), 3.61 (s, 3H), 1.93-1.91 (m, 2H), 1.78-1.45 (m, 6H), LC-MS (ESI) Calcd for C27H25NO5S [M+H]+: 475.14. Found: 475.80.
Sources & evidence
- ORD record
- ord-c5aae52d5cba468ea572577b93246cd9
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748632B2
Reaction notes
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