Ammonium Chloride → HCID 23114839, compound

HRID 748738Notes

Reaction equation

HRID 748738 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1.[F:14][C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1>[F:14][C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[CH:17]([OH:18])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 5642162-Bromo-5-methylpyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 23114839HCID 23114839, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, a tetrahydrofuran solution (1.5 ml, 3 mmol) of isopropylmagnesium chloride was added dropwise to a tetrahydrofuran (2 ml) solution of 2-bromo-5-methylpyridine (510 mg, 3 mmol) under ice cooling and the mixture was stirred at room temperature for 60 minutes. Under ice cooling, 2,5-difluorobenzaldehyde (328 μl, 3 mmol) was added dropwise to the resulting brown solution. The temperature of the reaction mixture was raised gradually to room temperature. A saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. After drying the solvent, the residue obtained by concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (130 mg, 18%) was obtained as an oil.

Workup

  1. temperatureThe temperature of the reaction mixture was raised gradually to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. customAfter drying the solvent
  4. customthe residue obtained by concentration under reduced pressure
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (130 mg, 18%)
  6. customwas obtained as an oil

Sources & evidence

ORD record
ord-c8337bb292ae4fc991e0e60f35953ebe
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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