反応 #11661

反応方程式

mono-boc-ortho-phenylenediamine

citric acid

6-cyano-nicotinic acid

N-methylmorpholine

isobutyl chloroformate

→

{2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

収率 78.3%

溶媒

DMF

反応条件

後処理

1. 1
   温度The reaction mixture was warmed to rt overnight
2. 2
   抽出The aqueous phase was extracted with ethyl acetate
3. 3
   洗浄the combined organic phases were washed with bicarbonate and brine
4. 4
   乾燥dried over Na2SO4
5. 5
   その他The solvent was evaporated

実験手順

To a solution of 444 mg (3.0 mmol) 6-cyano-nicotinic acid and 354 mg (3.5 mmol) N-methylmorpholine in 7 ml DMF at −20° C. was added 450 mg (3.3 mmol) isobutyl chloroformate. The reaction mixture was warmed to 5° C., and 625 mg (3.0 mmol) mono-boc-ortho-phenylenediamine was added. The reaction mixture was warmed to rt overnight and then poured into 50 ml 5% aqueous citric acid. The aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with bicarbonate and brine and dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (petrol ether/ethyl acetate 2:1) to yield 795 mg (2.35 mmol) {2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; mp.183–184° C.

出典