Sodium Chloride → HCID 71522918, compound

Participants

Reaction Steps

1-(3-{2-[3-(6-fluoropyridin-2-yl)pyrrolidin-1-yl]ethyl}pyridin-2-yl)piperidin-2-one a15-1 (32 mg, 0.087 mmol, 1 eq), 2,2,2-trifluoroethanol (13 mg, 0.13 mmol, 1.5 eq) and t-BuOK (48.8 mg, 0.43 mmol, 5 eq) are dissolved in DMSO. The reaction mixture is stirred at room temperature. After 2 hours, 2,2,2-trifluoroethanol (8.7 mg, 0.087 mmol, 1 eq) is added and the reaction mixture is stirred overnight. Ethyl acetate and aqueous saturated NaCl solution are then added, the two phases separated and the aqueous layer is reextracted with ethyl acetate (3 times). The organic layers are pooled, dried with MgSO4, filtered and condensed under reduced pressure. The residue is purified by basic reverse phase chromatography (gradient: water/acetonitrile/solvent C from 90/0/10 to 5/85/10 in 10 minutes; solvent C: acetonitrile/water 1/1+NH4CO3 0.4% w/v and NH4OH 0.05% v/v) to afford 11.7 mg of 1-[3-(2-{3-[6-(2,2,2-trifluoroethoxy)pyridin-2-yl]pyrrolidin-1-yl}ethyl)pyridin-2-yl]piperidin-2-one 108.

Provenance & Evidence