Sodium Bicarbonate → 2-(3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)benzonitrile

HRID 1616213Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1)#[N:14].C(=O)(O)[O-].[Na+]>CO.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:12][N:8]1[C:6]2=[N:7][C:2]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:13]#[N:14])=[CH:3][CH:4]=[C:5]2[NH:10][C:9]1=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

5-chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3) (74 mg, 0.4 mmol), 2-cyanophenylboronic acid pinacol ester (179 mg, 1.2 mmol), sodium bicarbonate (200 mg, 2.4 mmol), and bis(tri-t-butylphosphine)palladium(0) (61 mg, 0.12 mmol) were added to a microwave vial and purged with nitrogen. Dioxane (1.2 mL) was added, the vessel was sealed and the suspension was heated at 100° C. for 12 minutes in a microwave reactor. The cooled reaction was diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 2-(3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)benzonitrile (4-1). MS (M+H)+: observed=251.1, calculated=251.3.

Workup

custompurged with nitrogen
additionDioxane (1.2 mL) was added
customthe vessel was sealed
customThe cooled reaction
custompassed through a syringe
filtrationfilter
customThe solution was purified
customthe desired fractions were collected
concentrationconcentrated

Sources & evidence

ORD record: ord-8809cbeebcca4ac298a86b731081f01d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765784B2

Reaction notes

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