Hydrochloric Acid → 2-(2-Fluoro-4-vinylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

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Reaction Conditions

Reaction Steps

Trimethylsilylmethylmagnesium chloride, 1.1 M solution in THF (15 mL) was added dropwise to a solution at 0° C. of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde (4.00 g, 11 mmol) in THF (80 mL) and the reaction mixture was stirred for 30 min at 0° C. The reaction mixture was quenched with 1 N aq. HCl and extracted with EtOAc twice, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in THF (100 mL), and cooled to 0° C. in ice bath. The slurry of potassium t-butoxide (2.4 g, 21 mmol) in THF (12 mL) was added slowly. At the end of the addition the reaction mixture was allowed to stir for 30 min at 0° C. At this time 1 N HCl was added and the mixture was extracted with EtOAc and the organic layer was dried over MgSO4. The residue was concentrated in vacuo and purified by silica gel chromatography to afford 2-(2-fluoro-4-vinylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine. MS (ESI) m/z: calculated: 372.1; Observed: 373.0 (M++1).

Provenance & Evidence