Ammonium Chloride → HCID 23114591, compound

HRID 748741Notes

Reaction equation

HRID 748741 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, 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 2-bromo-3-methoxypyridine (564 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. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The solvent was dried, followed by concentration under reduced pressure to yield needle crystals. The resulting needle crystals were triturated with hexane, whereby the title compound (660 mg, 88%) was obtained.

Workup

  1. temperatureThe temperature of the reaction mixture was raised gradually to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. customThe solvent was dried
  4. concentrationfollowed by concentration under reduced pressure
  5. customto yield needle crystals
  6. customThe resulting needle crystals were triturated with hexane, whereby the title compound (660 mg, 88%)
  7. customwas obtained

Sources & evidence

ORD record
ord-0aa33bd0bec845c78a9fdb2d13883f13
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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