Diethyl Ether → HCID 72265020, compound

HRID 1270090Notes

Reaction equation

HRID 1270090 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) δ 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 C21H9F8N3O: 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-bc3281262a1f4c858cbede005d272265
Source dataset
uspto-grants-2007_04
Patent number
US07202232B2

Reaction notes

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