Imidazole → 3-[2-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide

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Reaction Steps

A solution of N-cyclopropyl-3-fluoro-5-[4-formyl-2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamide (Example 26e, 14.54 g) in DMF (120 mL) was treated with tert-butyldimethylchlorosilane (4.86 g) and imidazole (2.19 g) under nitrogen. The resulting mixture was stirred at room temperature for 1 h. More tert-butyldimethylchlorosilane (1.2 g) was added and the reaction mixture stirred at room temperature for 30 min, diluted with water (300 mL) and extracted with DCM (250 mL×2). The organics were dried (MgSO4), filtered and evaporated. The residue was purified (SiO2 chromatography, elution with 100% diethyl ether) to give the subtitle compound (15.20 g) as a gum.

Provenance & Evidence