Potassium tert-butoxide → 1,7-dimethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587602Notes

Reaction equation

[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:26]3=[N:27][CH:28]=[CH:29][C:30]([CH3:31])=[C:25]3[N:24]([CH3:32])[C:23]2=[O:33])=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>CC(N(C)C)=O.CO>[CH3:32][N:24]1[C:25]2[C:26](=[N:27][CH:28]=[CH:29][C:30]=2[CH3:31])[N:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][C:3]3[N:2]([CH3:1])[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[N:4]=3)=[CH:21][CH:20]=2)[C:23]1=[O:33]

Participants

Conditions

Temperature: 150 °C

Procedure

3-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (600 mg) was added to a solution of 3-(4-hydroxyphenyl)-1,7-dimethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (725 mg) and potassium tert-butoxide (351 mg) in DMA (4 ml) at 20° C. The mixture was stirred at 150° C. under a dry atmosphere for 30 min. 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 1,7-dimethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (150 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-64f97aecb84e49f488c70dd7d15e3d97
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226921B2

Reaction notes

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