Pyrazole → HCID 59161926, compound

HRID 216345Notes

Reaction equation

HRID 216345 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:12])[CH:9]([F:11])[F:10])=[N:6][CH:7]=1.[NH:13]1[CH:17]=[CH:16][CH:15]=[N:14]1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[F:10][CH:9]([F:11])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[CH:7][N:6]=1)=[O:12]

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86638499HCID 86638499, compound

Product 1

HCID 59161926HCID 59161926, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(5-bromopyridin-2-yl)-2,2-difluoroethanone (7.064 g, 30 mmol), pyrazole (1.85 g, 27 mmol), CuI (0.273 g, 1.4 mmol), racemic trans-N,N′-dimethylcyclohexane-1,2-diamine (0.714 g, 5 mmol), K2CO3 (7.894 g, 57 mmol) was added to a sealed tube and dissolved in toluene (12 mL). The mixture was stirred vigorously overnight at 110° C. The mixture was cooled and filtered through Celite, washing with EtOAc. The combined filtrate and washings were concentrated, flash chromatography on silica gel afforded the title compound as a white solid.

Workup

  1. additionwas added to a sealed tube
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through Celite
  4. washwashing with EtOAc
  5. concentrationThe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-7dbc48e555574b0c9ad8be7649a16f30
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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