Potassium tert-butoxide → 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((5-fluoro-2-thienyl)methoxy)pyridin-2(1H)-one

HRID 2203001Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH3:20])=[C:15]([CH:17]4[CH2:19][CH2:18]4)[N:16]=3)[CH:13]=2)[C:4](=[O:21])[CH:3]=1.[F:22][C:23]1[S:27][C:26]([CH2:28][OH:29])=[CH:25][CH:24]=1.CC(C)([O-])C.[K+]>COCCOC>[CH:17]1([C:15]2[N:16]=[C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH:6]=[CH:7][C:2]([O:29][CH2:28][C:26]5[S:27][C:23]([F:22])=[CH:24][CH:25]=5)=[CH:3][C:4]4=[O:21])=[CH:13][N:12]3[C:14]=2[CH3:20])[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (285 mg), (5-fluorothiophen-2-yl)methanol (109 mg), potassium tert-butoxide (93 mg) and DME (5 ml) was heated at 120° C. for 30 min under microwave irradiation. Additional potassium tert-butoxide (93 mg) and (5-fluorothiophen-2-yl)methanol (109 mg) in DME (0.5 ml) were added to the reaction mixture, and the resulting mixture was heated at 120° C. for further 30 min under microwave irradiation. The mixture was quenched with water and extracted with EtOAc/MeOH. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was crystallized from EtOH-IPA to give the title compound (120 mg) as an off-white solid.

Workup

temperaturethe resulting mixture was heated at 120° C. for further 30 min under microwave irradiation
customThe mixture was quenched with water
extractionextracted with EtOAc/MeOH
customThe organic layer was separated
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was crystallized from EtOH-IPA

Sources & evidence

ORD record: ord-e32db334dbeb4f6fbeb953f9b2be5293
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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