Ammonium Chloride → HCID 23114779, compound

HRID 2080359Notes

Reaction equation

HRID 2080359 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[C:11]([CH3:13])[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: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]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 27340872-Bromo-4-methylpyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 23114779HCID 23114779, compoundYield 65%

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-4-methylpyridine (334 μl, 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. The temperature of the resulting mixture was gradually raised to room temperature. After addition of a saturated aqueous solution of ammonium chloride, the resulting mixture was extracted with ethyl acetate. The solvent was then dried. The residue obtained by concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (456 mg, 65%) as needle crystals.

Workup

  1. temperatureThe temperature of the resulting mixture was gradually raised to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. customThe solvent was then dried
  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-8c740dce2fe14a8c86871043a840de67
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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