Ammonium Chloride → HCID 117760011, compound

HRID 1049604Notes

Reaction equation

HRID 1049604 reaction equation
[F:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[CH:12][C:11]=2[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[CH:12][C:11]=2[CH:26]([OH:31])[C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 117760004HCID 117760004, compound

Product 1

HCID 117760011HCID 117760011, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-(5-fluoro-2-methoxypyridin-4-yl)-5-((4-methoxybenzyl)oxy)phenyl)-2,2-dimethylpropan-1-one (270 mg) in methanol (5 mL) was added sodium borohydride (50 mg), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (255 mg) as a white amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ffa767a64621402db375742b4491a172
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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