Ammonium Chloride → HCID 23114695, compound

HRID 2080362Notes

Reaction equation

HRID 2080362 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, compoundYield 45.1%

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 the 3-allyloxy-2-bromopyridine (642 mg, 3 mmol) obtained in Referential Example 8 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 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 and the residue obtained by concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the title compound (375 mg, 45%) as an oil.

Workup

  1. customobtained in Referential Example 8 under ice cooling
  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. customthe residue obtained by concentration under reduced pressure
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9a0ef0f3aae44f69a0a47b02959681d6
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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