2,3-Difluoro-6-methoxyphenylboronic acid → 4-(2,3-Difluoro-6-methoxyphenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylic acid
Reaction equation
ClC1C=CC=C(F)C=1[C:9]1[N:10]=[C:11]([C:17]2[C:18]([CH3:26])=[N:19][N:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=23)[S:12][C:13]=1[C:14]([OH:16])=[O:15].[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[C:30]([O:35][CH3:36])[C:29]=1B(O)O>>[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[C:30]([O:35][CH3:36])[C:29]=1[C:9]1[N:10]=[C:11]([C:17]2[C:18]([CH3:26])=[N:19][N:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=23)[S:12][C:13]=1[C:14]([OH:16])=[O:15]Participants
3
Procedure
According to the similar manner described in Example 97-B (i) and (ii), the title compound (237 mg, 78%) has been obtained as a brown solid by the Suzuki coupling reaction followed by standard ester hydrolysis reaction using methyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-{[(trifluoromethyl)sulfonyl]oxy}-1,3-thiazole-5-carboxylate (339 mg, 0.805 mmol) obtained in Example 13-B (ii) and 2,3-difluoro-6-methoxyphenylboronic acid (303 mg, 1.61 mmol). The pure title compound has been obtained by washing with EtOAc (10 mL).
Sources & evidence
- ORD record
- ord-af4e493308864903a5956ca9508ab7ec
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139589B2
Reaction notes
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