反応 #168469

反応方程式

2-bromo-6-chloro-4-(1-cyclobutylethoxy)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine

(R)-3-phenylmorpholine

cesium fluoride

→

(3R)-4-(6-chloro-4-(1-cyclobutylethoxy)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-2-yl)-3-phenylmorpholine

溶媒

DMSO

water

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate (2×30 mL)
2. 2
   洗浄The combined organic extracts were washed with water (20 mL) and brine (20 mL)
3. 3
   乾燥dried over anhydrous Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by silica gel chromatography (eluting with 8-10% EtOAc/petroleum ether)

実験手順

To a solution of 2-bromo-6-chloro-4-(1-cyclobutylethoxy)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine (1.5 g, 3.40 mmol) in DMSO (15 mL), in a microwave tube was added (R)-3-phenylmorpholine (797 mg, 4.77 mmol) and cesium fluoride (3.6 g, 23.8 mmol). The reaction was heated at 125° C. in a microwave for 45 mins. The reaction was then diluted with water (50 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (eluting with 8-10% EtOAc/petroleum ether) to yield (3R)-4-(6-chloro-4-(1-cyclobutylethoxy)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-2-yl)-3-phenylmorpholine. MS ES/APCl calc'd. for C30H39ClN4O2 [M+H]+ 523. found 523.

出典