Potassium Carbonate → Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-2',5-difluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662523Notes

Reaction equation

HRID 1662523 reaction equation
[CH3:1][C:2]1([CH3:26])[C:6]([C:7]2[C:8](OS(C(F)(F)F)(=O)=O)=[CH:9][C:10]([F:17])=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH2:4][CH2:3]1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.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>[CH3:26][C:2]1([CH3:1])[C:6]([C:7]2[CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:10]([F:17])=[CH:9][C:8]=2[C:29]2[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:28]=2[F:27])=[CH:5][CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 57706168Methyl 5-(5,5-dimethylcyclopent-1-enyl)-2-fluoro-4-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 57706663Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-2',5-difluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 83.2F (1.05 g, 2.65 mmol) in DMF (5 mL) at 23° C. was added 2-fluoro-5-methoxyphenylboronic acid (0.90 g, 5.32 mmol) (commercially available from Aldrich) and potassium carbonate (1.10 g, 7.96 mmol) followed by tetrakis(triphenylphosphine)palladium (0.31 g, 0.27 mmol). The mixture was heated to 90° C. After 17 hours, the mixture was cooled to room temperature and then diluted with water. After extracting three times with EtOAc, the mixture was concentrated in vacuo and the residue was then purified on silica gel (0%-10% EtOAc/hexane) to give 83.2G as a clear oil that was used without further purification (0.92 g, 93%). 1H NMR (400 MHz, CDCl3) δ ppm 7.79 (1H, d, J=7.4 Hz), 7.13 (1H, d, J=11.3 Hz), 6.99 (1H, t, J=9.0 Hz), 6.84 (1H, dt, J=8.7, 3.7 Hz), 6.78 (1H, dd, J=5.9, 3.1 Hz), 5.55 (1H, s), 3.96 (3H, s), 3.79 (3H, s), 2.27 (2H, td, J=7.1, 2.5 Hz), 1.67 (2H, t, J=7.0 Hz), 0.84 (6H, s).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. extractionAfter extracting three times with EtOAc
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was then purified on silica gel (0%-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-8c60a413e1bd43d095a5976e853b889b
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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