N-methyl-2-pyrrolidone → HCID 10268983, compound

Participants

Reaction Conditions

Reaction Steps

A degassed mix of 7-chloro-5-isopropoxymethyl-5-(1,1-difluoroethyl)-5,10-dihydrobenzo[b][1,8]naphthyridine (21)(2.501 g, 7.089 mmol), Zn(CN)2 (849 mg, 7.089 mmol), Pd[P(t-Bu)3]2 (1.479 g, 2.836 mmol) and Zinc powder (556 mg, 8.507 mmol) in anhydrous NMP (20 mL) was heated at 170° C. for 22 h 30 min. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a pad of Celite and washed with EtOAc. The filtrate was washed with 2 N NH4OH (120 mL) and brine, dried over MgSO4, filtered and concentrated in vacuo. Flash chromatography (30%-50% EtOAc-Hexane) provided 22 (2.184 g, 90% yield) as a yellow solid: m.p. 134-135° C.; low resolution mass spectrum (ESI) m/z 344.3 [(M+H)+ calcd for C19H20F2N3O: 344.16].

Provenance & Evidence