tert-Butyl ((5-cyanopyridin-3-yl)methyl)carbamate synthesis

Yield:1108724-20-4 86%

Reaction Conditions:

Stage #1: 3-bromo-5-(tert-butoxycarbonyl)aminomethylpyridine;dicyanozinc;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 110; for 3 h;
Stage #2: with ammonia in diethyl ether;water;N,N-dimethyl-formamide;

Steps:

1.1.82

To tert-butyl (5-bromopyridin-3-yl)methylcarbamate (384 mg, 1.34 mmol) in DMF (10 ml), Zn(CN)₂ (94 mg, 0.80 mmol) and Pd(PPh₃)₄ were added and heated at 110⁰C for 3h. Then the reaction mixture was cooled to RT, diluted with ether, washed with ammonium hydroxide solution, water and brine. Crude residue was column chromatographed (40%ethylacetate/60%Hexanes) to yield tert-butyl (5-cyanopyridin-3-yl)methylcarbamate in 86% yield.

References:

WO2009/42694,2009,A1 Location in patent:Page/Page column 119