Dimethylformamide → Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

HRID 1662517Notes

Reaction equation

HRID 1662517 reaction equation
C1([C@H](C2C=CC=C(OC[C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[C:27](OC)[CH:26]=[CH:25][C:24]=4F)=[C:19]([C@H:32](O)C(C)(C)C=C)[CH:18]=3)C=2)CC(O)=O)CC1.[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([F:49])=[C:44](B(O)O)[CH:45]=1.[C:50](=[O:53])([O-])[O-:51].[K+].[K+].[CH3:56]N(C=O)C>[Cl-].[Na+].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>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([F:49])=[C:44]([C:28]2[CH:27]=[CH:26][C:25]([C:50]([O:51][CH3:56])=[O:53])=[CH:24][C:23]=2[C:20]2[C:19]([CH3:18])([CH3:32])[CH2:17][CH2:22][CH:21]=2)[CH:45]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acidHCID 57705953HCID 57705953, compound

Product 1

HCID 57706006Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-(trifluoromethylsulfonyloxy)benzoate 66.61 (0.100 g, 0.3 mmol) in DMF (4 mL) at 23° C. was added 5-chloro-2-fluorophenylboronic acid (0.07 g, 0.4 mmol) (commercially available from Aldrich), potassium carbonate (0.1 g, 0.8 mmol), followed by tetrakis(triphenylphosphine)palladium (0.03 g, 0.03 mmol). The mixture was heated to 90° C. and stirring was continued for 23 hours. The reaction was then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-10% EtOAc in hexanes) to yield 78.9A as a colorless oil (0.082 g, 86% yield).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a7ebf87dedfc42cfbb1ef9bfaa7ba955
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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