Water → 3-benzyloxy-5-[4-(N,N-dimethylamino)phenyl]-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole

HRID 2102337Notes

Reaction equation

HRID 2102337 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:12](Br)[N:11]([CH:25]([CH3:27])[CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:44][N:45](C)[CH:46]=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:13]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:12]([C:31]2[CH:32]=[CH:33][C:28]([N:45]([CH3:46])[CH3:44])=[CH:29][CH:30]=2)[N:11]([CH:25]([CH3:27])[CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 230795293-Benzyloxy-5-bromo-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole

Product 1

HCID 669711163-benzyloxy-5-[4-(N,N-dimethylamino)phenyl]-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
80 °C

Procedure

A suspension of 3-benzyloxy-5-bromo-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole (0.11 g), 4-N,N-dimethylamino)-phenylboronic acid (0.061 g), tetrakis(triphenylphosphine)-palladium (0.034 g), potassium carbonate (0.078 g) and water (0.2 mL) in N,N-dimethylformamide (4 mL) was stirred at 80° C. for 12 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent:hexane/ethyl acetate=5/1) to give the title compound (0.098 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on aminopropylated silica gel (eluent:hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-74bd8968a7f74da8bfa6abbb48444e0e
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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