Sodium hydride → (6-(2-Fluorophenyl)pyridin-3-yloxy)acetic acid methyl ester

HRID 1896700Notes

Reaction equation

HRID 1896700 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.[CH3:17][O:18][C:19](=[O:22])[CH2:20]Br>CN(C=O)C>[CH3:17][O:18][C:19](=[O:22])[CH2:20][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

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 231457706-(2-Fluorophenyl)pyridin-3-ol

Product 1

HCID 69105901(6-(2-Fluorophenyl)pyridin-3-yloxy)acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 157.3 mg (3.6 mmol) of sodium hydride (55% suspension in mineral oil) were added to 620 mg (3.27 mmol) of 6-(2-fluorophenyl)pyridin-3-ol in 25 ml of DMF. After stirring at room temperature for 60 min, 551.4 mg (3.6 mmol) of bromoacetic acid methyl ester were added, and the reaction mixture was stirred at room temperature for 2 h. After concentrating, water was added, and the mixture was extracted with ethyl acetate. The organic phase was separated and concentrated. Yield: 687 mg (80%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. concentrationAfter concentrating
  3. additionwater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic phase was separated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c07216efc7e74890927c2c941a4b9e87
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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