Sodium borohydride → [3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methanol

HRID 228750Notes

Reaction equation

HRID 228750 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[OH:24])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57756468[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methanone2×

Product 1

HCID 57756348[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl-methanone (55 mg) (compound 220) was dissolved in methanol (3 ml) to prepare a solution. Sodium borohydride (26 mg) was added to the solution at 0° C., and the mixture was stirred at room temperature for 2 hr. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give the title compound (52 mg, yield 92%).

Workup

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was then washed with saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-2dac512f58c54d378732a3788ebc9450
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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