1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57837497, compound

HRID 731722Notes

Reaction equation

HRID 731722 reaction equation
Cl[CH:2]([CH3:14])[C:3](=[O:13])[C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[I-].[NH2:16][N+:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]2[C:4]([C:3](=[O:13])[CH2:2][CH3:14])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 86637279HCID 86637279, compound

Product 1

HCID 57837497HCID 57837497, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 8.7 g (38 mmol) of 4-chloro-1-(4-fluorophenyl)pent-1-yn-3-one and 10 g (45 mmol) of N-aminopyridinium iodide in 140 ml of acetonitrile was added dropwise 11 g of DBU in 50 ml of acetonitrile at 0° C. for 20 minutes under a nitrogen atmosphere. The reaction was then stirred at RT overnight. After evaporation of the solvent, the crude mixture was purified on an Al2O3 column, and the desired product recrystallized from ethyl acetate-hexane to obtain 200 mg of 1-(2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)propan-1-one. Compound 1070.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude mixture was purified on an Al2O3 column
  3. customthe desired product recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d3f6233a5d0e4f488b3135c2a5f94e30
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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