Diethyl Ether → HCID 72265020, compound

HRID 645961Notes

Reaction equation

HRID 645961 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)[N:4]=1.[F:22][C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=1[C:30](=[O:34])[CH2:31][C:32]#[N:33].C(O)(=O)C.N1CCCCC1.CCOCC>C1C=CC=CC=1>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[N:5]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[C:31]([C:30](=[O:34])[C:24]3[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=3[F:22])[C:32]#[N:33])=[CH:14][CH:13]=2)[N:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9793820Piperidine, acetateHCID 184490243-(2,3-Difluorophenyl)-3-oxopropanenitrileHCID 18449038HCID 18449038, compound

Product 1

HCID 72265020HCID 72265020, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 4-(3,5-bis-trifluoromethyl-pyrazol-1-yl)-benzaldehyde (0.18 g, 0.58 mmol), 3-(2,3-difluoro-phenyl)-3-oxo-propionitrile (0.1 g, 0.55 mmol) and piperidine acetate (8 mg, 0.06 mmol) in dry benzene was heated at reflux for 12 hours. Volatile components were removed under reduced pressure to give a syrup. Trituration with ether gave 3-[4-(3,5-bis-trifluoromethyl-pyrazol-1-yl)-phenyl]-2-(2,3-difluoro-benzoyl)-acrylonitrile (0.18 g, 65% yield) as a solid: 1H-NMR (CDCl3) 6δ 7.15 (s, 1H), 7.24-7.32 (m, 1H), 7.38-7.50 (m, 2H), 7.72 (d, 2H, J=8.4), 8.11 (s, 1H), 8.20 (d, 2H, J=8.4) ppm. ESMS calculated for C21 H9F8N3O: 471.1; Found: 472.0 (M+H)+.

Workup

  1. temperatureat reflux for 12 hours
  2. customVolatile components were removed under reduced pressure
  3. customto give a syrup

Sources & evidence

ORD record
ord-035ba71c66c946359c04e21e0f96f33a
Source dataset
uspto-grants-2010_04
Patent number
US07705029B2

Reaction notes

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