Dimethylformamide → HCID 58993529, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-Butyl 4-(3-bromophenyl)-4-(((4′-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)piperidine-1-carboxylate (150 mg, 0.238 mmol), zinc cyanide (33.6 mg, 0.286 mmol), palladium tetrakis triphenylphosphine (27.5 mg, 0.024 mmol), and dimethylformamide (1 mL) was charged to a conical vial and purged with nitrogen for 5 minutes. The vial was sealed and heated at 120° C. for 2 hours and then held at room temperature overnight. The resulting mixture was filtered through a syringe tip filter and applied directly to a silica gel column. Gradient elution with 5-40% ethyl acetate/hexanes afforded the product as a clear oil (83 mg, 61%). 1H-NMR (CDCl3, 500 MHz) δ ppm 7.76 (m, 2H), 7.68 (s, 1H), 7.56-7.64 (m, 4H), 7.45-7.49 (m, 1H), 7.38-7.43 (m, 2H), 7.34 (s, 1H), 3.69 (m, 2H), 3.45 (s, 2H), 3.05 (m, 2H), 2.10 (m, 2H), 1.88 (m, 2H), 1.42 (s, 9H). Mass spec.: 576.17 (MH)+.

Provenance & Evidence