Sodium hydride → [6-(2-Fluoro-phenyl)-pyridin-3-yloxy]-acetic acid tert-butyl ester

HRID 1931435Notes

Reaction equation

HRID 1931435 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[C:17]([O:21][C:22](=[O:25])[CH2:23]Br)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22](=[O:25])[CH2:23][O:16][C:13]1[CH:14]=[N:15][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[F:3])=[CH:11][CH:12]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 231457706-(2-Fluorophenyl)pyridin-3-ol

Product 1

HCID 68536675[6-(2-Fluoro-phenyl)-pyridin-3-yloxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 63.4 mg (1.45 mmol) of sodium hydride (55% in mineral oil) were added to 250 mg (1.32 mmol) of 6-(2-fluoro-phenyl)-pyridin-3-ol in 10 ml of DMF. The mixture was stirred at room temperature for 60 min. Then 283.5 mg (1.45 mmol) of bromoacetic acid tert-butyl ester were added, and the reaction mixture was stirred at room temperature for 2 h. After evaporation, water was added, and the mixture was extracted with ethyl acetate. The combined extracts were dried and concentrated. Yield: 311 mg.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. customAfter evaporation, water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe combined extracts were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-69bc613b1ac44c9180363b7519e21135
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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