[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[C:21](OC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1SC(C2C=C(F)C=CC=2F)=NC=1C(OCC)=O)C1C=CC=CC=1.[Li+].[BH4-]>C1COCC1>[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH2:21][OH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a solution of a mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate and ethyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate (7.8 g, 21.70 mmol) in THF (72.3 mL) was slowly added LiBH4 (0.946 g, 43.4 mmol) at room temperature. The reaction mixture was stirred for overnight. After quenched with water, the reaction mixture was extracted with EtOAc. The organic layers was washed with saturated NaHCO3 solution and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography to yield (5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)methanol (6.66 g, 97%) as white solid. LC/MS (uplc): MH+ 318.2, 1.03 min.
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