Sodium Bicarbonate → N-(4-(1,4-dihydroxy-2-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide
Reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([NH:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[O:19])[CH:7]=[CH:8][C:9]=1[C:10](=[O:16])[C:11]([CH2:13][CH2:14][OH:15])=[CH2:12].C(=O)(O)[O-].[Na+]>CO>[OH:16][CH:10]([C:9]1[CH:8]=[CH:7][C:6]([NH:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[O:19])=[CH:5][C:4]=1[F:3])[CH:11]([CH3:12])[CH2:13][CH2:14][OH:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
150 mg of sodium borohydride was added to a methanol (8 ml) solution of 320 mg of N-(3-fluoro-4-(2-(2-hydroxyethyl)acryloyl)phenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at room temperature for 1 hour. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, 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: chloroform/methanol=100/1) to obtain the entitled compound as a colorless oily substance.
Workup
- customthe reaction liquid
- extractionextracted with chloroform
- dry with materialdried with anhydrous sodium sulfate
- customThe solvent was evaporated away under reduced pressure
- customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
- customto obtain the entitled compound as a colorless oily substance
Sources & evidence
- ORD record
- ord-8f009ebd2be44ea9909ab57463635e3f
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728025B2
Reaction notes
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