Ammonium Chloride → HCID 23114839, compound

HRID 2080358Notes

Reaction equation

HRID 2080358 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, compoundYield 18.4%

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 tetrahydrofuran (2 ml) solution of 2-bromo-5-methylpyridine (510 mg, 3 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 60 minutes. To the resulting brown solution was added dropwise 2,5-difluorobenzaldehyde (328 μl, 3 mmol) under ice cooling and then, the temperature of the reaction mixture was raised to room temperature gradually. A saturated aqueous solution of ammonium chloride was added to the reaction mixture and then, 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) to give the title compound (130 mg, 18%) as an oil.

Workup

  1. temperaturethe temperature of the reaction mixture was raised to room temperature gradually
  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)

Sources & evidence

ORD record
ord-708bd08e9c2f4137bd6159bd7c25e91a
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…