3-Bromopyridine → HCID 12127979, compound

HRID 748743Notes

Reaction equation

HRID 748743 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, 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 ml) solution of 3-bromopyridine (286 μl, 3 mmol) under ice cooling. The resulting 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 raised gradually to room temperature. To the reaction mixture was added a saturated aqueous solution of ammonium chloride and then, the mixture was extracted with ethyl acetate. The solvent was dried, followed by concentration under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=1:1), whereby the title compound (296 mg, 45%) was obtained as needle crystals.

Workup

  1. temperatureThe temperature of the reaction mixture was raised gradually to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe solvent was dried
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=1:1), whereby the title compound (296 mg, 45%)
  7. customwas obtained as needle crystals

Sources & evidence

ORD record
ord-18e5190e270d41b8a16982567a51a7dc
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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