Ammonium Chloride → 1-(3-Phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethanol

HRID 243045Notes

Reaction equation

HRID 243045 reaction equation
[BH4-].[Na+].[C:3]1([N:9]2[C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[C:18](=[O:20])[CH3:19])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-].[NH4+]>CO>[C:3]1([N:9]2[C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH:18]([OH:20])[CH3:19])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 681577931-(3-Phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethanone

Product 1

HCID 681574131-(3-Phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethanolYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.27 g, 7.17 mmol) was added to a stirred suspension of 1-(3-phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethanone (0.85 g, 3.58 mmol) in methanol (20 mL) at 0° C. under nitrogen. The reaction mixture was stirred for 15 minutes then poured into saturated aqueous ammonium chloride solution and extracted with EtOAc (3×50 mL). The combined EtOAc extracts were washed with water, dried (Na2SO4) and concentrated in vacuo to give the title compound as a white solid (0.74 g, 87%). LCMS (method H): Rt 1.76 min, [M+H]+ 240.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined EtOAc extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91ed4a81a9364729b0f502ec606fda43
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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