Sodium hydride → HCID 17757773, compound

Participants

Reaction Steps

To a solution of 100 mg (0.252 mmol) 1′-[(6-chloro-1H-indol-3-yl)carbonyl]spiro[3,1-benzoxazine-4,4′-piperidin]-2(1H)-one (described in example 1) in dry DMF (5 ml) was added 10 mg NaH (0.25 mmol, 60% in oil). After 15 minutes at RT, 43.9 mg (0.277 mmol) of 3-fluoro-benzoyl chloride was added and stirring continued overnight. The reaction mixture was poured onto an aqueous solution of ammonium chloride, and the product extracted twice with ethyl acetate. The combined organic phases were dried on Na2SO4 and the solvent evaporated under reduced pressure. Purification by preparative HPLC yielded 1′-{[6-chloro-1-(3-fluorobenzoyl)-1H-indol-3-yl]carbonyl}spiro[3,1-benzoxazine-4,4′-piperidin]-2(1H)-one.

Provenance & Evidence