Cesium carbonate → HCID 54760300, compound

HRID 1616211Notes

Reaction equation

HRID 1616211 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:16])[C:9](=[O:15])[N:10]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:5]2=[CH:4][CH:3]=1.[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B1OC(C)(C)C(C)(C)O1)#[N:18].C(=O)([O-])[O-].[Cs+].[Cs+]>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>[CH:12]1([CH2:11][N:10]2[C:5]3[C:6](=[N:7][C:2]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[C:17]#[N:18])=[CH:3][CH:4]=3)[N:8]([CH3:16])[C:9]2=[O:15])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 35702292-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 772308275-chloro-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 54760300HCID 54760300, compound

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

5-chloro-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-4) (35 mg, 0.138 mmol), 2-cyanophenylboronic acid pinacol ester (79 mg, 0.345 mmol), cesium carbonate (135 mg, 0.414 mmol), and bis(tri-t-butylphosphine)palladium(0) (7 mg, 0.014 mmol) were added to a microwave vial, and purged with nitrogen. Dioxane (1.1 ml) and water (0.3 ml) were added and the suspension was heated at 90° C. overnight. 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 2-[1-(cyclopropylmethyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]benzonitrile (1-5). HRMS (M+H)+: observed=305.1403, calculated=305.1397.

Workup

  1. custompurged with nitrogen
  2. additionDioxane (1.1 ml) and water (0.3 ml) were added
  3. temperatureThe reaction was cooled to room temperature
  4. additiondiluted with methanol
  5. custompassed through a syringe
  6. filtrationfilter
  7. customThe solution was purified
  8. customthe desired fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b7899bb2d6a64a75a2324dbd7735a2b6
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

Loading…