Ammonium Chloride → HCID 23114710, compound

HRID 748737Notes

Reaction equation

HRID 748737 reaction equation
C([Mg][Cl:5])(C)C.Br[C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[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.[Cl-].[NH4+]>O1CCCC1>[ClH:5].[Cl:5][CH:17]([C:16]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:15]=1[F:14])[C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 2208322-Bromo-3-methylpyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 23114710HCID 23114710, 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 (2.0 ml) solution of 2-bromo-3-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 then raised gradually to room temperature. After addition of a saturated aqueous solution of ammonium chloride, the resulting 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=8:1) to yield a mixture containing the title compound. To the resulting mixture were added thionyl chloride (2.0 ml) and a drop of dimethylformamide, followed by stirring at room temperature for 14 hours. Distillation of excess thionyl chloride under reduced pressure yielded a white precipitate. The resulting white precipitate was triturated with hexane and diethyl ether, whereby the title compound (101 mg, 12%) was obtained.

Workup

  1. temperatureThe temperature of the reaction mixture was then raised gradually to room temperature
  2. extractionthe resulting 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=8:1)
  6. customto yield a mixture

Sources & evidence

ORD record
ord-511efb1f8797427b9dcfde3ec931313a
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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