Potassium Carbonate → HCID 67170195, compound

HRID 1475770Notes

Reaction equation

HRID 1475770 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)=[C:6](Br)[CH:5]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27].C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:22]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:20]([Cl:19])[CH:21]=2)[C:7]([O:10][CH:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)=[CH:8][CH:9]=1)=[O:18]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 32475223-Chloro-4-methoxybenzeneboronic acidHCID 67169821HCID 67169821, compound

Product 1

HCID 67170195HCID 67170195, compoundYield 50.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

150 mg of 3-Bromo-4-(3,3-difluoro-cyclobutoxy)-benzoic acid methyl ester, 113 mg of 3-chloro-4-methoxyphenylboronic acid, 129 mg K2CO3, 10 mg of palladium(II)acetate, and 25 mg of triphenylphosphine were dissolved using 10 ml of DMF and 0.5 ml of water. The reaction mixture was stirred at 120° C. for 2 h, then cooled to room temperature, 50 ml of water added and extracted three times using 30 ml of EA each. The organic layer was dried using MgSO4 and volatiles were evaporated. Chromatography on silica gel using EA/HEP 1:5 yielded 90 mg of the title compound, viscous oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted three times
  3. customThe organic layer was dried
  4. customwere evaporated

Sources & evidence

ORD record
ord-f56e79d0862a4208945c151fd6731168
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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