Tributylphosphine → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((5-(difluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one

HRID 2203074Notes

Reaction equation

[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[F:22][C:23](F)([F:31])[C:24]1[S:28][C:27]([CH2:29]O)=[CH:26][CH:25]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:29][C:27]5[S:28][C:24]([CH:23]([F:31])[F:22])=[CH:25][CH:26]=5)=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (78 mg), (5-(trifluoromethyl)-2-thienyl)methanol (77 mg) and tributylphosphine (168 mg) in THF (3 ml) was added 1,1′-(azodicarbonyl)dipiperidine (210 mg), and the reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOH-hexane to give the title compound (48.5 mg) as a white solid.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc
customThe resulting solid was recrystallized from EtOH-hexane

Sources & evidence

ORD record: ord-2af8f068a99f4d00b3fa42ecbdda6e28
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

Loading…