Sodium Bicarbonate → N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-4-hydroxybutanoyl)-3-fluorophenyl)pyridine-2-carboxamide

HRID 13383Notes

Reaction equation

HRID 13383 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])=[CH:9][C:8]=1[F:22].[Si:23]([O:30][CH:31]1[CH2:35][CH2:34][O:33][C:32]1=[O:36])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>O1CCCC1>[Si:23]([O:30][CH:31]([CH2:35][CH2:34][OH:33])[C:32]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])=[CH:9][C:8]=1[F:22])=[O:36])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 50462413-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-oneHCID 23145244N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamideHCID 178418339Butyllithium

Product 1

HCID 67482856N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-4-hydroxybutanoyl)-3-fluorophenyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.1 ml of n-butyl lithium (2.66 M hexane solution) was dropwise added to a tetrahydrofuran (100 ml) solution of 1.1 g of N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamide at −78° C., and the reaction liquid was stirred at the same temperature for 15 minutes. 1.21 g of 3-((t-butyl(dimethyl)silyl)oxy)dihydrofuran-2 (3H)-one was added to the reaction liquid, and the reaction liquid was stirred at the same temperature for 1 hour. Aqueous saturated sodium bicarbonate solution was added to the reaction liquid at the same temperature, then heated up to room temperature and extracted with ethyl acetate. The organic layer was 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

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at the same temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
  8. customto obtain the entitled compound as a colorless oily substance

Sources & evidence

ORD record
ord-5792d20b11a24431869bed1f57a12458
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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