Ammonium Chloride → HCID 23114591, compound

HRID 2080361Notes

Reaction equation

HRID 2080361 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][N:8]=1.[F:15][C:16]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:17]=1[CH:18]=[O:19].[Cl-].[NH4+]>O1CCCC1>[F:15][C:16]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:17]=1[CH:18]([OH:19])[C:7]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 903642-Bromo-3-methoxypyridineHCID 1376632,5-DifluorobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 23114591HCID 23114591, compoundYield 88%

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-3-methoxypyridine (564 mg, 3 mmol) under ice cooling. The reaction mixture was then stirred at room temperature for 60 minutes. To the resulting brown solution, 2,5-difluorobenzaldehyde (328 μl, 3 mmol) was added dropwise under ice cooling. The temperature of the reaction 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. After the solvent was dried, needle crystals obtained by concentration under reduced pressure were triturated with hexane to give the title compound (660 mg, 88%).

Workup

  1. temperatureThe temperature of the reaction mixture was gradually raised to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. customAfter the solvent was dried
  4. customneedle crystals obtained by concentration under reduced pressure
  5. customwere triturated with hexane

Sources & evidence

ORD record
ord-bb70fda0cb3742e7ad6d3d4e1a26155f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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