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

HRID 2202983Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (150 mg), (5-chlorothiophen-3-yl)methanol (174 mg) and tributylphosphine (358 mg) in THF (15 ml) was added 1,1′-(azodicarbonyl)dipiperidine (447 mg), and the mixture was stirred at 60° C. for 4 h. The reaction mixture was then cooled to room temperature, and concentrated in vacuo. The residue was diluted with DCM (100 ml), washed with water and brine successively, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (MeOH/DCM) to afford the title compound (90 mg) as a white solid.

Workup

temperatureThe reaction mixture was then cooled to room temperature
concentrationconcentrated in vacuo
additionThe residue was diluted with DCM (100 ml)
washwashed with water and brine successively
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-d3c6cb8a71c145aa97cf54dd75cb3b2c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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