Cesium carbonate → 5-(4-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1616229Notes

Reaction equation

HRID 1616229 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=1[CH3:16])(=O)=O.[CH3:19][C:20]([CH3:37])([CH3:36])[CH2:21][N:22]1[C:30]2[C:25](=[N:26][C:27](B(O)O)=[CH:28][CH:29]=2)[N:24]([CH3:34])[C:23]1=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CO.Cl[Cu].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([C:27]2[N:26]=[C:25]3[N:24]([CH3:34])[C:23](=[O:35])[N:22]([CH2:21][C:20]([CH3:19])([CH3:37])[CH3:36])[C:30]3=[CH:29][CH:28]=2)=[C:8]([CH3:16])[CH:9]=1)(=[O:15])[CH3:14]

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 213024274-Acetyl-2-methylphenyl trifluoromethanesulfonateHCID 86691828[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]boronic acid

Product 1

HCID 866918435-(4-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave vial, 4-acetyl-2-methylphenyl trifluoromethanesulfonate (34-1) (40 mg, 0.14 mmol), [1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]boronic acid (14-1) (56 mg, 0.22 mmol), cesium carbonate (92 mg, 0.28 mmol), CuCl (14 mg, 0.14 mmol), and Bis(diphenylphosphino)ferrocene dicholoropalladium (8 mg, 0.015 mmol) was added under nitrogen and dissolved in DMF (0.7 ml). The suspension was heated overnight at 100° C. The reaction was cooled to room temperature, 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 5-(4-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (34-2). MS (M+H)+: observed=352.3, calculated=352.4.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. custompassed through a syringe
  3. filtrationfilter
  4. customThe solution was purified
  5. customthe desired fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf2b679205c44509b6513e4d1e20764b
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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