Dimethylformamide → HCID 178519658, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (0.22 g, 60% dispersion in oil, 5.5 mmol) in anhydrous THF (20 mL) under argon atmosphere was added 3-bromo-5-chloro-pyridin-2-ol (1.03 g, 5 mmol) in a portionwise manner. After hydrogen evolution had ceased the mixture was cooled to −78° C. and tert-butyl lithium (10 mmol) was added at such a rate that the temperature did not rise above −65° C. The mixture was stirred for 5 mins then DMF (15 mmol) was added keeping the temperature below −50° C. The mixture was allowed to warm to room temperature and partitioned between ethyl acetate and 1N HCl. The organic layer was separated, washed with saturated NaCl, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound (300 mg).

Provenance & Evidence