Ammonium Chloride → HCID 23114710, compound

HRID 2080357Notes

Reaction equation

HRID 2080357 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. The resulting mixture was stirred at room temperature for 60 minutes. To the resulting brown solution, 2,5-difluorobenzaldehyde (328 μl, 3 mmol) was added dropwise under ice cooling. The temperature of the reaction mixture was then raised to room temperature gradually. After addition of a saturated aqueous solution of ammonium chloride, the resulting mixture was extracted with ethyl acetate. After the solvent was dried, the residue obtained by concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=8:1) to give a mixture containing the title compound. Thionyl chloride (2.0 ml) and one drop of dimethylformamide were added to the mixture. The resulting mixture was stirred at room temperature for 14 hours. Excess thionyl chloride was distilled off under reduced pressure to yield a white precipitate. The resulting precipitate was triturated with hexane and diethyl ether to give the title compound (101 mg, 12%).

Workup

  1. temperatureThe temperature of the reaction mixture was then raised to room temperature gradually
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. customAfter the solvent was dried
  4. customthe residue obtained by concentration under reduced pressure
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=8:1)
  6. customto give a mixture

Sources & evidence

ORD record
ord-c7539586ccbb4254951bfe14869b312a
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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