Formic Acid → HCID 86680742, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(6-bromo-pyridin-3-yl)-5,5-dimethyl-pyrazolidin-3-one (Example 12, step 1) (800 mg, 2.96 mmol) and formic acid (0.57 ml, 14.8 mmol, 5 equiv.) in water (8 ml) was heated to 100° C. At this temperature formaldehyde (36% in water) (1.13 ml, 14.8 mmol, 5 equiv.) was added drop wise. The mixture was stirred overnight at 100° C. The reaction mixture was cooled and basified carefully with 2N NaOH and extracted two times with a small amount of dichloromethane. The organic layers were loaded directly on a silica gel column and the crude product was purified by flash chromatography eluting with a heptane:ethyl acetate gradient 100:0 to 0:100. The desired 2-(6-bromo-pyridin-3-yl)-1,5,5-trimethyl-pyrazolidin-3-one (380 mg, 45% yield) was obtained as a colorless oil, MS: m/e=284.3/286.3 (M+H+).

Provenance & Evidence