Methanol → HCID 22387906, compound

HRID 1699830Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[O:20][CH3:21])[C:9]([CH3:11])=[N:10][C:5]2=[CH:4][CH:3]=1.CN(C)[CH:24]=[O:25].C(N(CC)CC)C.[C]=O.[CH3:36][OH:37]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:8]2[C:6]3=[N:7][C:2]([C:36]([O:25][CH3:24])=[O:37])=[CH:3][CH:4]=[C:5]3[N:10]=[C:9]2[CH3:11])=[C:14]([O:20][CH3:21])[CH:15]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 5-bromo-3-(4-chloro-2-methoxybenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (200 mg) in anhydrous methanol (1.8 ml) and an anhydrous N,N-dimethylformamide (2 ml) were added anhydrous triethylamine (129 mg), palladium acetate (35 mg) and 1,3-bis(diphenylphosiphino)propane (72 mg) and the mixture was placed in an autoclave. After replacing with carbon monoxide 4 times, the mixture was stirred at 85° C. and 10 atm. After 18 hr, the reaction mixture was cooled and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with water (three times) and saturated brine, then dried over anhydrous magnesium sulfate. The residue was subjected to flash silica gel chromatography (silica gel, 40 ml, eluent: dichloromethane-methanol=50-1) and crystallized from ethanol to give the objective compound (148 mg) as pale-yellow crystals.

Workup

temperaturethe reaction mixture was cooled
extractionThe mixture was extracted with ethyl acetate
washThe organic layer was washed with water (three times) and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customcrystallized from ethanol

Sources & evidence

ORD record: ord-4bfd81f79fb742b1a884f5eb91db5ffa
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348474B1

Reaction notes

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