反应 #273

反应方程式

CONC(=O)c1ccccc1Nc1c

Cc1cc(N)n(C(C)C)n1

→

CONC(=O)c1ccccc1Nc1c

收率 47.8%

溶剂

C1COCCO1

反应条件

实验过程

2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (134 mg, 0.96 mmol) and cesium carbonate (626 mg, 1.92 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (39.9 mg, 0.06 mmol) and diacetoxypalladium (7.19 mg, 0.03 mmol) were added and tube was sealed. Mixture was stirred at reflux overnight. Reaction was allowed to cool to room temperature, filtered, washed with CH2Cl2/MeOH (9/1, 10 mL). Silica (63-200 µm) was added to the filtrate and mixture was concentrated to dryness. The crude product was purified by flash chromatography (dry loading) on silica gel eluting with 1 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford 2-(5-chloro-2-(1-isopropyl-3-methyl-1H-pyrazol-5-ylamino)pyridin-4-ylamino)-N-methoxybenzamide (127 mg, 47.8 %) as a pale beige foam => _contaminated by a few BINAP or BINAP by-products_

来源