Triphenylphosphine → 2-{3-methyl-1-[(1-methylcyclopropyl)methyl]-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl}benzonitrile
Reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])=[CH:9][CH:10]=[C:5]2[NH:4][C:3]1=[O:19].[CH3:20][C:21]1([CH2:24]O)[CH2:23][CH2:22]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])=[CH:9][CH:10]=[C:5]2[N:4]([CH2:20][C:21]2([CH3:24])[CH2:23][CH2:22]2)[C:3]1=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)benzonitrile (4-1) (50 mg, 0.2 mmol), 1-methylcyclopropanemethanol (52 mg, 0.6 mmol), Diisopropyl azodicarboxylate (121 mg, 0.6 mmol), and triphenylphosphine (157 mg, 0.6 mmol) were added to a microwave vial under nitrogen and dissolved with DCM (1 mL). The reaction was stirred for one hour, and desired product was observed via LCMS. The mixture was diluted with methanol and purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile); the desired fractions were collected and concentrated to produce 2-{3-methyl-1-[(1-methylcyclopropyl)methyl]-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl}benzonitrile (4-2). HRMS (M+H)+: observed=319.1551, calculated=319.1553.
Sources & evidence
- ORD record
- ord-fbecca7e97614b1eb6ae32a6c51bfae1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765784B2
Reaction notes
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