benzyl 4-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate → 4-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)piperidine

HRID 2196537Notes

Reaction equation

HRID 2196537 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([C:17]3[CH2:22][CH2:21][N:20](C(OCC4C=CC=CC=4)=O)[CH2:19][CH:18]=3)[CH:14]=[CH:15][CH:16]=2)[N:9]=[C:8]([C:33]([F:36])([F:35])[F:34])[CH:7]=1.[H][H]>CO.[Pd]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)[N:9]=[C:8]([C:33]([F:34])([F:35])[F:36])[CH:7]=1

Participants

5

Reactant 2

HCID 59843270benzyl 4-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 598433184-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)piperidineYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 64 (430 mg, 0.871 mmol) in MeOH (4.4 mL) was added palladium on carbon (9.27 mg, 0.087 mmol). Under a balloon of hydrogen the suspension was allowed to stir for 2 h. It was then filtered and filtrate evaporated. The crude was used without any further purification. The title product 65 (315 mg, 100% yield) was isolated as a colorless oil. LRMS (ESI): calc. 361.4; found 362.5 (MH)+.

Workup

  1. filtrationIt was then filtered
  2. customfiltrate evaporated
  3. customThe crude was used without any further purification

Sources & evidence

ORD record
ord-5e5001a98cb84ff8a073b83d92099c1c
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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