Water → HCID 13216500, compound

HRID 910247Notes

Reaction equation

HRID 910247 reaction equation
[N:1]1[C:2]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH3:18][Mg]Br.[Cl-].[NH4+].O>O1CCCC1>[N:1]1[C:2]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]([OH:15])[CH3:18])=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 8209634-imidazo[1,2-a]pyridin-2-ylbenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 13216500HCID 13216500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Subsequently, 4-imidazo[1,2-a]pyridin-2-ylbenzaldehyde g) was dissolved in tetrahydrofuran (100 mL), followed by stirring under ice cooling. Methyl magnesium bromide (3.0M diethyl ether solution, 4.4 mL) was added dropwise to the reaction mixture, followed by stirring at room temperature for 1 hour. Saturated aqueous ammonium chloride solution (5 mL) was added dropwise to the reaction mixture, followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with chloroform, followed by drying over magnesium sulfate. The solvent was evaporated, and the solid was recovered through filtration by use of dichloromethane-methanol (30:1) mixture. The filtrate was concentrated under reduced pressure, and the residue was subjected to flash chromatography. Fractions eluted by dichloromethane-methanol (30:1) were concentrated under reduced pressure, and the solid was recovered through filtration by use of diethyl ether. Through the above procedure, 1-(4-imidazo[1,2-a]pyridin-2-ylphenyl)-1-ethanol (2.43 g) was yielded.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. stirringby stirring at room temperature for 1 hour
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialby drying over magnesium sulfate
  5. customThe solvent was evaporated
  6. filtrationthe solid was recovered through filtration by use of dichloromethane-methanol (30:1) mixture
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washFractions eluted by dichloromethane-methanol (30:1)
  9. concentrationwere concentrated under reduced pressure
  10. filtrationthe solid was recovered through filtration by use of diethyl ether

Sources & evidence

ORD record
ord-36c3d2c99514407fb4a5709f1982401b
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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