1-Methylimidazole → HCID 57340965, compound

Participants

Reaction Conditions

Reaction Steps

TsCl (275 mg, 1.44 mmol) and N-methylimidazole (285 uL, 3.60 mmol) were added at 0° C. to a suspension of 2-fluoro-nicotinic acid (169 mg, 1.20 mmol) in CH2Cl2 (3 mL) under Ar atmosphere. The mixture was stirred at 0° C. for 1 hour. Compound R (195 mg, 1.00 mmol) was added to the mixture at 0° C. over 5 minutes and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. N-methylimidazole (47.5 uL, 0.60 mmol) and TsCl (114 mg, 0.60 mmol) were added at 0° C. to the mixture, and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was washed with saturated NaHCO3 (aq.), water (5 times) and brine. The organic phase was then dried over anhydrous Na2SO4 and concentrated in vacuo to afford compound S (300 mg, 1.00 mmol) as a white powder.

Provenance & Evidence