HCID 59327161, compound → HCID 59326992, compound

HRID 410311Notes

Reaction equation

HRID 410311 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH2:12][CH2:11][C:10]([C:14]([F:17])([F:16])[F:15])([OH:13])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>O1CCCC1.[Pd]>[F:1][C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][C:10]([C:14]([F:15])([F:16])[F:17])([OH:13])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 59327161HCID 59327161, compound

Product 1

HCID 59326992HCID 59326992, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 3-(2-fluoropyridin-3-yl)-1-(trifluoromethyl)cyclopent-2-enol (940 mg, 3.80 mmol) in tetrahydrofuran (35 mL) was treated with palladium, 10% wt. on activated carbon (202 mg, 0.190 mmol). The reaction mixture was purged through 3 vacuum-hydrogen cycles, and was stirred under hydrogen at 23° C. After 18 h, the reaction was filtered through celite and the filter cake was washed with tetrahydrofuran (50 mL). The combined filtrates were concentrated, affording the product as a yellow oil. MS (ESI, pos. ion) m/z: 250.0 (M+1).

Workup

  1. customThe reaction mixture was purged through 3 vacuum-hydrogen cycles
  2. filtrationthe reaction was filtered through celite
  3. washthe filter cake was washed with tetrahydrofuran (50 mL)
  4. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-0bfe1bf9e1b6497aa563237ba9d7b31e
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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