Lithium iodide → 3'-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)-4-methoxybiphenyl-3-carboxylic acid
Reaction equation
C1(N2C(=O)C3C=CC(OCC4C=C(B(O)O)C=CC=4)=CC=3S2)CCCC1.IC1C=CC(OC)=C(C=1)C(OC)=O.[CH:40]1([N:45]2[C:49](=[O:50])[C:48]3[CH:51]=[CH:52][C:53]([O:55][CH2:56][C:57]4[CH:58]=[C:59]([C:63]5[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[C:65]([C:71]([O:73]C)=[O:72])[CH:64]=5)[CH:60]=[CH:61][CH:62]=4)=[CH:54][C:47]=3[S:46]2)[CH2:44][CH2:43][CH2:42][CH2:41]1.[Li+].[I-]>N1C=CC=CC=1>[CH:40]1([N:45]2[C:49](=[O:50])[C:48]3[CH:51]=[CH:52][C:53]([O:55][CH2:56][C:57]4[CH:58]=[C:59]([C:63]5[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[C:65]([C:71]([OH:73])=[O:72])[CH:64]=5)[CH:60]=[CH:61][CH:62]=4)=[CH:54][C:47]=3[S:46]2)[CH2:41][CH2:42][CH2:43][CH2:44]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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), methyl 5-iodo-2-methoxybenzoate (0.056 g, 0.20 mmol) were coupled according to the general procedure and the resulting methyl 3′-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)-4-methoxybiphenyl-3-carboxylate was hydrolyzed using LiI (0.019 g, 0.14 mmol) in refluxing pyridine (2 mL) to afford the title product. The crude residue was purified using automated prep-HPLC to yield the desired compound as a pale yellow solid (0.013 g, over two steps 10%). δ1 NMR (400 MHz, CDCl3): δ 8.44 (s, 1H), 7.87 (d, 1H, J=8.2 Hz), 7.89 (d, 1H, J=8.7 Hz), 7.63 (s, 1H), 7.58 (d, 1H, J=7.8 Hz), 7.49 (t, 1H, J=7.8 Hz), 7.41-7.39 (m, 1H), 7.28-7.24 (m, 2H), 7.14 (d, 1H, J=8.7 Hz), 5.26 (s, 2H), 4.63-4.59 (m, 1H), 3.89 (s, 3H), 2.16-2.04 (m, 2H), 2.04-1.58 (m, 6H). LC-MS (ESI) Calcd for C27H25NO5S [M+H]+: 475.14. Found: 475.80.
Sources & evidence
- ORD record
- ord-17d94c0398704f7699efe7add50cc8ca
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748632B2
Reaction notes
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