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

HRID 1662444Notes

Reaction equation

HRID 1662444 reaction equation
[F:1][CH:2]([F:27])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[C:19]2[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH:20]=2)[CH:8]=1>CO.CCOC(C)=O.[Pd]>[F:27][CH:2]([F:1])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH:19]2[CH2:20][CH2:21][CH2:22][C:23]2([CH3:24])[CH3:25])[CH:8]=1

Participants

5

Reactant 1

HCID 57705519Methyl 5'-(difluoromethyl)-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57705984Methyl 5'-(difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-carboxylateYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dry flask containing 66.50B (0.8621 g, 2.303 mmol) in dry MeOH (10 mL) and EtOAc (2 mL) was added palladium (10% wt. on activated carbon) (0.2455 g, 0.2307 mmol). After purging, the mixture was stirred under an atmosphere of hydrogen at room temperature. The reaction was monitored with TLC and LC-MS. After 22.5 hours, the reaction was filtered through Celite. After concentration, the residue was identified as 66.51A and was used without purification (863 mg, 99% yield). MS ESI (pos.) m/e: 376.9 (M+H)+.

Workup

  1. customAfter purging
  2. filtrationthe reaction was filtered through Celite
  3. concentrationAfter concentration
  4. customwas used without purification (863 mg, 99% yield)

Sources & evidence

ORD record
ord-8b9adff88bcc49dd84850de23d45f451
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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