Potassium Carbonate → 4-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde

HRID 1520630Notes

Reaction equation

HRID 1520630 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[CH:7]=[O:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[N:4][N:5]([CH3:9])[C:6]=2[CH:7]=[O:8])=[CH:13][CH:12]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27946344-bromo-1-methyl-1H-pyrazole-5-carbaldehyde

Product 1

HCID 866425044-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde (0.500 g), 4-chlorophenylboronic acid (0.455 g), tetrabutylammonium bromide (0.853 g), potassium carbonate (0.914 g) and palladium acetate (0.030 g) were stirred together in 5 mL of water and heated to 45° C. After stirring for 2.5 hours, the reaction was diluted with ethyl acetate (75 mL) and washed with water (25 mL), brine (50 mL), dried over magnesium sulfate, filtered and concentrated to give the crude material. The solid was chromatographed over silica gel (SF40-80) eluted using a gradient of 5% to 25% ethyl acetate/hexanes over 30 minutes.

Workup

  1. washwashed with water (25 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b96ef7ac38f44587bd23361b67ed3e7c
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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