Toluene → HCID 118468237, compound

HRID 629321Notes

Reaction equation

HRID 629321 reaction equation
[Cl:1][C:2]1[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:21])[CH:3]=1.C1(C)C=CC=CC=1.Br[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH:41]=[CH:40][CH:39]=[N:38]2)=[CH:33][CH:32]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O.C(O)C>[N:37]1([C:34]2[CH:35]=[CH:36][C:31]([CH2:30][C:11]3[C:2]([Cl:1])=[CH:3][C:4]([OH:21])=[C:5]([CH:10]=3)[C:6]([O:8][CH3:9])=[O:7])=[CH:32][CH:33]=2)[CH:41]=[CH:40][CH:39]=[N:38]1

Participants

9

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 27764791-[4-(Bromomethyl)Phenyl]-1H-PyrazoleHCID 75486482HCID 75486482, compound

Product 1

HCID 118468237HCID 118468237, compoundYield 37.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-chloro-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.15 g) in a mixed solvent of toluene (4.00 mL)-ethanol (0.80 mL)-water (0.80 mL) were added 1-(4-(bromomethyl)phenyl)-1H-pyrazole (0.11 g), tetrakis(triphenylphosphine)palladium(0) (0.06 g) and tripotassium phosphate (0.26 g), and the mixture was stirred overnight at 100° C. under argon atmosphere. The reaction mixture was allowed to be cooled to room temperature, water and ethyl acetate were added thereto, and the mixture was partitioned. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.06 g).

Workup

  1. temperatureto be cooled to room temperature
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7d49c3da837c4ba191fded6158c83b07
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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