Water → N-(3-Pyrazolo[1,5-a]pyridin-3-yl-phenyl)-acetamide

HRID 1093521Notes

Reaction equation

HRID 1093521 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.[C:11]([NH:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)(=[O:13])[CH3:12].C([O-])([O-])=O.[K+].[K+].O>C1(C)C=CC=CC=1.CO.CCO.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>[N:4]1[N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2=[C:2]([C:19]2[CH:20]=[C:15]([NH:14][C:11](=[O:13])[CH3:12])[CH:16]=[CH:17][CH:18]=2)[CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 27557863-Bromo-pyrazolo[1,5-a]pyridine

Product 1

HCID 66592668N-(3-Pyrazolo[1,5-a]pyridin-3-yl-phenyl)-acetamideYield 19.9%

Reagents, catalysts & solvents 4

HCID 178418851HCID 178418851, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 3-bromo-pyrazolo[1,5-a]pyridine (197 mg, 1 mmol), (3-acetylaminophenyl)boronic acid (179 mg), K2CO3 (6 eq) and bis(tri-t-butylphosphine)palladium (0) (5 mg) in PhMe (1 ml), MeOH (1 ml), EtOH (1 ml), and H2O (1.8 ml) was stirred and heated at 155° C. in the microwave for 30 minutes. The mixture was partitioned between EtOAc/H2O. The layers were separated and the organic layer was dried, filtered and evaporated. The residue was crystallised from MeOH to give the title compound (50 mg). MS: [M+H]+ 252

Workup

  1. customThe mixture was partitioned between EtOAc/H2O
  2. customThe layers were separated
  3. customthe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallised from MeOH

Sources & evidence

ORD record
ord-0ed27c2bec9143e0a9c72ae02b6f3221
Source dataset
uspto-grants-2012_03
Patent number
US08131527B1

Reaction notes

Loading…