Tributylphosphine → 4-((5-Chloro-3-thienyl)methoxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2202889Notes

Reaction equation

[CH2:1]([C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[C:10]([N:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]3=[O:20])[CH:11]=[CH:12][C:5]=2[N:4]=1)[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:19][C:16]2[CH:17]=[CH:18][N:13]([C:10]3[CH:11]=[CH:12][C:5]4[N:4]=[C:3]([CH2:1][CH3:2])[N:7]([CH3:8])[C:6]=4[CH:9]=3)[C:14](=[O:20])[CH:15]=2)[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (126 mg), (5-chloro-3-thienyl)methanol (139 mg) and tributylphosphine (0.347 ml) in THF (8 ml) was added 1,1′-(azodicarbonyl)dipiperidine (354 mg), and the mixture was stirred at 60° C. for 2 h. The reaction mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried MgSO4, and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc to MeOH/EtOAc). The resulting solid was recrystallized from EtOH/hexane to give the title compound (90 mg) as a white solid.

Workup

customThe reaction mixture was partitioned between EtOAc and water
washthe organic layer was washed with brine, dried MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc to MeOH/EtOAc)
customThe resulting solid was recrystallized from EtOH/hexane

Sources & evidence

ORD record: ord-84643a51136b44a68996ad7d7c66c271
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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