Water → Methyl 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoate

HRID 1096980Notes

Reaction equation

HRID 1096980 reaction equation
Br[C:2]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH3:17].[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:16]([O:15][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:12][CH2:13][CH3:14])[C:2]=1[C:22]1[CH:21]=[N:20][N:19]([CH3:18])[CH:23]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57930905Methyl 4-bromo-3,5-diethoxybenzoate

Product 1

HCID 57930985Methyl 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178506421HCID 178506421, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-bromo-3,5-diethoxybenzoate (1 g) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (895 mg) were dissolved in DME in a nitrogen atmosphere, and potassium phosphate (2.1 g) and 1,1′-bis(diphenylphosphino)ferrocene palladium (D) chloride-CH2Cl2 complex (269 mg) were added to it at room temperature, and degassed. The reaction liquid was stirred overnight at 90° C., then cooled to room temperature, and water was added to it, and this was filtered through Celite. The filtrate was extracted with chloroform, washed with saturated saline water, and dried with sodium sulfate. Sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 50/50 to 35/65) to obtain the title compound as a pale yellow solid.

Workup

  1. additionwere added to it at room temperature
  2. customdegassed
  3. customThe reaction liquid
  4. temperaturecooled to room temperature
  5. filtrationthis was filtered through Celite
  6. extractionThe filtrate was extracted with chloroform
  7. washwashed with saturated saline water
  8. dry with materialdried with sodium sulfate
  9. customSodium sulfate was removed through filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 50/50 to 35/65)

Sources & evidence

ORD record
ord-27647d87145c4f04a979401548d5c6d7
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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