Sodium hydride → 6-chloro-1-ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587523Notes

Reaction equation

Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]2[N:21]([CH2:22][CH3:23])[C:20](=[O:24])[N:19]([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[C:16]2=[N:17][CH:18]=1.[H-].[Na+]>CN(C=O)C.CO>[Cl:12][C:13]1[CH:14]=[C:15]2[N:21]([CH2:22][CH3:23])[C:20](=[O:24])[N:19]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:2]4[N:6]([CH3:7])[C:5]5[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=5[N:3]=4)=[CH:27][CH:26]=3)[C:16]2=[N:17][CH:18]=1

Participants

Conditions

Temperature: 180 °C

Procedure

2-Chloro-1-methyl-1H-benzimidazole (50 mg) was added to a solution of 6-chloro-1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (90 mg) and NaH (13.2 mg) in DMF (2 mL) at room temperature. The mixture was heated at 180° C. for 30 min under microwave irradiation. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 6-chloro-1-ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (100 mg) as colorless crystals.

Workup

concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane)

Sources & evidence

ORD record: ord-62da0e3a4b3140b496782d7950730880
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226921B2

Reaction notes

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