Tetrabutylammonium Fluoride → 4-((1RS,2RS)-2-(4-chlorophenyl)cyclopropyl)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203080Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:10]([Si](C)(C)C)[CH:9]2[C:15]2[CH:20]=[CH:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]4[N:28]=[C:27]([CH:29]5[CH2:31][CH2:30]5)[N:26]([CH3:32])[C:25]=4[CH:33]=3)[C:17](=[O:34])[CH:16]=2)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:15]2[CH:20]=[CH:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]4[N:28]=[C:27]([CH:29]5[CH2:31][CH2:30]5)[N:26]([CH3:32])[C:25]=4[CH:33]=3)[C:17](=[O:34])[CH:16]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-((1RS,2RS)-2-(4-chlorophenyl)-3-(trimethylsilyl)cyclopropyl)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (26 mg), TBAF (1.0 M in THF, 0.533 ml) and THF (1 ml) was heated at 100° C. under microwave irradiation for 1 h. The mixture was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (9.2 mg) as a white solid.

Workup

customThe mixture was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-0766468e6d8a4f01938388a53c656625
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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