3-Bromopyridine → HCID 12127979, compound

HRID 2080363Notes

Reaction equation

HRID 2080363 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[F:13][C:14]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:15]=1[CH:16]=[O:17].[Cl-].[NH4+]>O1CCCC1>[F:13][C:14]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:15]=1[CH:16]([OH:17])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 12127979HCID 12127979, compoundYield 45%

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 3-bromopyridine (286 μl, 3 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 60 minutes. To the resulting brown solution thus obtained was added dropwise 2,5-difluorobenzaldehyde (328 μl, 3 mmol) under ice cooling. The temperature of the reaction mixture was gradually raised to room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The solvent was then dried. The residue remaining after concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give the title compound (296 mg, 45%) as needle crystals.

Workup

  1. customTo the resulting brown solution thus obtained
  2. temperatureThe temperature of the reaction mixture was gradually raised to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. customThe solvent was then dried
  5. concentrationafter concentration under reduced pressure
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5e4181a7188a41ce9a261c29b2220688
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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