Ammonium Chloride → HCID 66778670, compound

HRID 2090829Notes

Reaction equation

HRID 2090829 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=2)[N:3]=1.O1CCCC1.[CH:24]1([Mg]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[Cl-].[NH4+]>O1CCCC1>[CH:24]1([CH:7]([C:6]2[C:2]([CH3:1])=[N:3][N:4]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][N:10]=3)[CH:5]=2)[OH:8])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 43324083HCID 43324083, compoundHCID 178420632HCID 178420632, compound

Product 1

HCID 66778670HCID 66778670, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carbaldehyde (2.6 g) synthesized above in tetrahydrofuran (40 mL) was added dropwise 1M cyclohexylmagnesium bromide tetrahydrofuran solution (15 mL) at 0° C. After stirring at 0° C. for 1 hr, aqueous ammonium chloride solution was added, 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=1:4, volume ratio) to give the title object compound (2.0 g, 36%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe extract was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record
ord-415b24c6aa4c45f4acf492ebfb58b0e9
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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