Lithium borohydride → 4-{5-Chloro-2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile

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Reaction Conditions

Reaction Steps

4-{5-Chloro-2-[(1,1-dimethyl-2-oxoethyl)amino]-1,3-thiazol-4-yl}benzonitrile (1.15 g, 3.76 mmol), prepared in the previous step, was dissolved in tetrahydrofuran (20 mL) and cooled to 0° C. Lithium borohydride (2M in tetrahydrofuran; 2.25 mL, 2.5 mmol) was added dropwise and the mixture was stirred for 1 h. The reaction was quenched with saturated NH4Cl, diluted with ethyl acetate and washed with H2O, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (20% acetone/hexane) afforded 4-{5-chloro-2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (1.01 g, 88%) as a white solid. HRMS: calcd for C14H14ClN3OS+H+, 308.06188; found (ESI, [M+H]+), 308.0612; Analytical HPLC: purity 100% at 210-370 nm, 10.0 min; 100% at 252 nm, 10.0 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence