反応 #2290159

反応方程式

1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one

(5-(trifluoromethyl)thiophen-2-yl)methanol

tributylphosphine

1,1′-(azodicarbonyl)dipiperidine

→

title compound

収率 20.2%

1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((5-(trifluoromethyl)thiophen-2-yl)methoxy)pyridin-2(1H)-one

収率 20.2%

溶媒

water

THF

反応条件

後処理

1. 1
   温度the mixture was heated at the same temperature for 2 h
2. 2
   抽出extracted with EtOAc
3. 3
   洗浄The extract was washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   濃縮concentrated
6. 6
   その他purified by NH silica gel column chromatography (hexane/EtOAc)
7. 7
   その他The resulting solid was purified by preparative HPLC (C18, mobile phase: H2O/CH3CN (0.1% TFA included))
8. 8
   抽出extracted with EtOAc
9. 9
   その他The organic layer was separated
10. 10
    乾燥dried over MgSO4
11. 11
    濃縮concentrated in vacuo

実験手順

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (100 mg), (5-(trifluoromethyl)thiophen-2-yl)methanol (130 mg) and tributylphosphine (0.27 ml) in THF (10 ml) was added 1,1′-(azodicarbonyl)dipiperidine (269 mg) at 60° C., and the mixture was heated at the same temperature for 2 h. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated, and purified by NH silica gel column chromatography (hexane/EtOAc), followed by silica gel column chromatography (EtOAc/MeOH). The resulting solid was purified by preparative HPLC (C18, mobile phase: H2O/CH3CN (0.1% TFA included)). The desired fraction was neutralized with saturated NaHCO3 solution, and extracted with EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo to give the title compound (32.0 mg) as a white solid.

出典