Ammonium Chloride → HCID 23114695, compound

HRID 748742Notes

Reaction equation

HRID 748742 reaction equation
C([Mg]Cl)(C)C.[CH2:6]([O:9][C:10]1[C:11](Br)=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:7]=[CH2:8].[F:17][C:18]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:19]=1[CH:20]=[O:21].[Cl-].[NH4+]>O1CCCC1>[CH2:6]([O:9][C:10]1[C:11]([CH:20]([C:19]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:18]=2[F:17])[OH:21])=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:7]=[CH2:8]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 230285742-Bromo-3-[(prop-2-en-1-yl)oxy]pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 23114695HCID 23114695, 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-allyloxy-2-bromopyridine (642 mg, 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. A saturated aqueous solution of ammonium chloride was added 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=4:1), whereby the title compound (375 mg, 45%) was obtained as an oil.

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=4:1), whereby the title compound (375 mg, 45%)
  7. customwas obtained as an oil

Sources & evidence

ORD record
ord-1353757dff7948859cf8bb7118787a4f
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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