4-Methyl-3-cyanopyridine → HCID 178428388, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6 M, 3.33 mL, 0.00534 mol) was added slowly for a period of 5 min at a temperature of at −78° C. to a solution of 5-fluoro-pyridin-2-ylamine (0.3 g, 0.00267 mol) in anhydrous tetrahydrofuran (20 mL). Then the temperature raised to −40° C. and the reaction mixture was stirred for 15 min. The reaction mixture was cooled to −78° C. and 4-methyl-nicotinonitrile (0.316 g, 0.00267 mol) in tetrahydrofuran (5 mL) was added. The temperature was raised to RT and stirred for 18 h. The reaction mixture quenched with a saturated aqueous ammonium chloride solution (25 mL) and then extracted with ethyl acetate (2×50 mL). The combined organic layer were dried over sodium sulphate and concentrated under vacuum to afford the crude product, N-(5-fluoro-pyridin-2-yl)-4-methyl-nicotinamidine, which was used without further purification in the next step. MS (M+1): 231.1.

Provenance & Evidence