HCID 67111742, compound → 1-(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)-1-(3,3-difluorocyclobutyl)-2-(trimethylsilyl)ethanol

Participants

Reaction Conditions

Reaction Steps

Trimethylsilylmethylmagnesium chloride (1.1M solution in THF; 2.24 mL, 2.47 mmol) was added to a solution of (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)(3,3-difluorocyclobutyl)methanone (630 mg, 1.450 mmol) in THF (30.0 mL) at 25° C., and the resulting solution was stirred at 25° C. for 10 min. Excess Grignard reagent was quenched by the careful addition of sat. aq. NH4Cl (10 mL), water was added to dissolve the precipitated salts, and THF was then removed in vacuo. The resulting mixture was partitioned between EtOAc (250 mL) and sat. aq. NH4Cl (50 mL), and the organic layer was separated and washed with brine (50 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to provide 1-(2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)-1-(3,3-difluoro-cyclobutyl)-2-(trimethylsilyl)ethanol as a yellow foam. MS (ESI) m/z: Calculated: 522.2; Observed: 522.8 (M++1).

Provenance & Evidence