Tributylphosphine → 4-((5-Chlorothiophen-3-yl)methoxy)-1-(2-ethyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

HRID 2202992Notes

Reaction equation

[CH2:1]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]3=[O:18])=[CH:7][N:6]2[C:19]=1[CH3:20])[CH3:2].[Cl:21][C:22]1[S:26][CH:25]=[C:24]([CH2:27]O)[CH:23]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[Cl:21][C:22]1[S:26][CH:25]=[C:24]([CH2:27][O:17][C:14]2[CH:15]=[CH:16][N:11]([C:8]3[CH:9]=[CH:10][C:5]4[N:6]([C:19]([CH3:20])=[C:3]([CH2:1][CH3:2])[N:4]=4)[CH:7]=3)[C:12](=[O:18])[CH:13]=2)[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-ethyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (150 mg), (5-chlorothiophen-3-yl)methanol (165 mg) and tributylphosphine (340 mg) in THF (15 ml) was added 1,1′-(azodicarbonyl)dipiperidine (424 mg), and the mixture was stirred at 60° C. for 5 h. The reaction mixture was cooled to room temperature, concentrated in vacuo, and diluted with DCM. The mixture was washed with water and brine successively, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (MeOH/DCM) to afford the title compound (60 mg) as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
additiondiluted with DCM
washThe mixture was washed with water and brine successively
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-d18516ab4f9f47e8b3b2edfd00e38874
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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