Dimethylformamide → Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662509Notes

Reaction equation

HRID 1662509 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.[CH3:39][O:40][C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=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>[CH3:32][C:19]1([CH3:18])[C:20]([C:23]2[CH:24]=[C:25]([C:50]([O:51][CH3:56])=[O:53])[CH:26]=[CH:27][C:28]=2[C:43]2[CH:44]=[CH:45][CH:46]=[C:41]([O:40][CH3:39])[CH:42]=2)=[CH:21][CH2:22][CH2:17]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 57705953HCID 57705953, compound

Product 1

HCID 57707227Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 66.61 (1.00 g, 2.6 mmol) in DMF (15.00 mL) at 23° C. was added 3-methoxyphenylboronic acid (0.80 g, 5.3 mmol) (commercially available from Aldrich), potassium carbonate (1.1 g, 7.9 mmol), and then tetrakis(triphenylphosphine)palladium (0.31 g, 0.26 mmol). The mixture was heated to 90° C. and stirred for 18 hours. The reaction was then cooled to room temperature, 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. The resulting product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 78.5A as a colorless oil (0.80 g, 90% 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 resulting product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6606b383a71f491584192c0025d2895a
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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