Ammonium Chloride → N-(3-fluoro-4-(1-hydroxy-3-methyl-3-buten-1-yl)phenyl)pyridine-2-carboxamide

HRID 13426Notes

Reaction equation

HRID 13426 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[O:18])[CH:7]=[CH:8][C:9]=1[C:10](=[O:15])[CH2:11][C:12]([CH3:14])=[CH2:13].[Cl-].[NH4+]>CO>[F:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[O:18])[CH:7]=[CH:8][C:9]=1[CH:10]([OH:15])[CH2:11][C:12]([CH3:14])=[CH2:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23145243N-(3-fluoro-4-(3-methyl-3-butenoyl)phenyl)pyridine-2-carboxamide

Product 1

HCID 23145600N-(3-fluoro-4-(1-hydroxy-3-methyl-3-buten-1-yl)phenyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

88.8 mg of sodium borohydride was added to a methanol (5 ml) solution of 280 mg of N-(3-fluoro-4-(3-methyl-3-butenoyl)phenyl)pyridine-2-carboxamide. The reaction liquid was stirred at room temperature for 3 hours, and then poured into an aqueous saturated ammonium chloride solution, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1) to obtain the entitled compound.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was evaporated away under reduced pressure
  5. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1)
  6. customto obtain the entitled compound

Sources & evidence

ORD record
ord-3f3cb1c020834c45a87b5331f0312cf0
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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