HCID 86761825, compound → HCID 86761824, compound

HRID 2090966Notes

Reaction equation

HRID 2090966 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[C:11]([CH2:16][CH3:17])=[N:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:18]1([Mg]Br)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH:18]1([CH:14]([C:12]2[C:11]([CH2:16][CH3:17])=[N:10][N:9]([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=3)[CH:13]=2)[OH:15])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 86761825HCID 86761825, compound2×HCID 178419651HCID 178419651, compound

Product 1

HCID 86761824HCID 86761824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (10 mL) of 1-(3,5-difluorophenyl)-3-ethyl-1H-pyrazole-4-carbaldehyde (1.5 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise under ice-cooling cyclohexylmagnesium bromide (12.0 mL, 1M tetrahydrofuran solution). After the completion of the dropwise addition, the ice bath was removed, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (1.9 g, quantitative) as a pale-yellow oil.

Workup

  1. additionwas added dropwise under ice-
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. additionTo the reaction mixture was added aqueous ammonium chloride solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)
  8. customto give the title object compound (1.9 g, quantitative) as a pale-yellow oil

Sources & evidence

ORD record
ord-49ed10d9ec1145e08d21f699d16c5cb5
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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