Water → HCID 67405279, compound

HRID 910213Notes

Reaction equation

HRID 910213 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[CH3:19][Mg]Br.[Cl-].[NH4+].O>O1CCCC1>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]([OH:16])[CH3:19])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 16738347HCID 16738347, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67405279HCID 67405279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(6-Iodoimidazo[1,2-a]pyridin-2-yl)benzaldehyde (820 mg) was dissolved in tetrahydrofuran (25 mL), and the solution was stirred under ice cooling. Methyl magnesium bromide (787 mL) was added dropwise to the reaction mixture, followed by stirring for 15 minutes under ice cooling and then for 5 hours at room temperature. Aqueous saturated ammonium chloride solution (25 mL) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with dichloromethane-methanol. Subsequently, the solvent was evaporated, and the residue was purified through silica gel column chromatography (dichloromethane:methanol=97:3), followed by concentration under reduced pressure, to thereby yield the title compound (579 mg).

Workup

  1. stirringby stirring for 15 minutes under ice cooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionfollowed by extraction with dichloromethane-methanol
  4. customSubsequently, the solvent was evaporated
  5. customthe residue was purified through silica gel column chromatography (dichloromethane:methanol=97:3)
  6. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-8d350c617a5d4288af05aaffc194c8b8
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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