Trifluoroacetic acid → 4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,7-dihydro-5H-cyclopenta[c]pyridine

HRID 714053Notes

Reaction equation

HRID 714053 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2O[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[CH:17]1[CH2:21][CH2:20][CH2:19][CH:18]=1.FC(F)(F)C(O)=O.C(N(CC)CC)C>ClC1C=CC=CC=1Cl>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:18]3[CH2:19][CH2:20][CH2:21][C:17]=3[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 8882CyclopenteneHCID 86699311Oxazole, 5-[3-fluoro-4-(trifluoromethyl)phenyl]-

Product 1

HCID 898462994-[3-fluoro-4-(trifluoromethyl)phenyl]-6,7-dihydro-5H-cyclopenta[c]pyridineYield 44%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 5-(3-fluoro-4-(trifluoromethyl)phenyl)-oxazole (0.50 g, 2.16 mmol), cyclopentene (2.95 g, 43.3 mmol) and trifluoroacetic acid (0.49 g, 4.33 mmol) in o-dichlorobenzene (12 mL) was heated under microwave irradiation to 220° C. for 6 h. To the reaction mixture was added triethylamine (5 mL) and the solvent mixture removed under reduced pressure. Purification by flash chromatography (70 g SiO2, Telos-cartridge) eluting with a 0 to 50% EtOAc/n-heptane gradient provided the title compound (266 mg, 44%) as a slightly brown solid. MS: 282.5 (M+H)+.

Workup

  1. customthe solvent mixture removed under reduced pressure
  2. customPurification by flash chromatography (70 g SiO2, Telos-cartridge)
  3. washeluting with a 0 to 50% EtOAc/n-heptane gradient

Sources & evidence

ORD record
ord-d644277edb8a4a1db46a631f1b91f0bd
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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