Tetrahydrofuran → HCID 57690673, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dibromopyridine (16.92 g, 71.4 mmol) and 2-amino-3-cyanopyridine (5.0 g, 42.0 mmol) in THF (150 ml) was cooled to below −30° C. before n-butyl lithium (33.6 ml, 84 mmol, 2.5 M in hexanes) was added dropwise while maintaining temperature below −30° C. On complete addition, the reaction mixture was stirred at 0° C. on an ice bath for 1.5 hours. The reaction was then quenched by the addition of 2 M HCl (until pH=˜1) while keeping the temperature below 15° C., and stirred at below 15° C. for 15 mins. Additional 2M HCl (50 ml) was added and the mixture extracted with EtOAc (2×150 ml), the acidic aqueous was cooled on an ice bath before being basified by addition of 2M NaOH, causing precipitation of a brown solid. Resulting suspension was left to stand overnight, then solid product collected by filtration, washed with water and dried by suction, then under high vacuum to leave crude title compound as a brown solid (6.52 g, 56%). 1H NMR (DMSO-d6) 6.65 (1H, dd), 7.79 (2H, s), 7.93-7.83 (4H, m), 7.99 (1H, t), 8.28 (1H, dd). ES+ 280.80.

Provenance & Evidence