Sodium hydride → HCID 178448674, compound

Participants

Reaction Steps

step 5—To a solution of the pyrazolone 62a (300 mg, 1.1 mmol) in THF (5 mL) was added NaH (54 mg, 1.4 mmol). The reaction mixture was stirred at RT for 20 min, and 3-chloro-benzo[d]isothiazole 1,1-dioxide (270 mg, 1.4 mmol) was added. The reaction mixture was then stirred at RT for 2 h, quenched with saturated aqueous NH4Cl and extracted into ethyl acetate (2×). The combined organics were dried (MgSO4), filtered and the solvent was removed under reduced pressure. The crude product was purified by reverse-phase column chromatography eluting with acetonitrile/water which afforded 15 mg (3%) of III-2; LCMS RT 2.3 min, M−H.

Provenance & Evidence