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Sodium hydride → [6-(4-Fluoro-phenyl)-pyridin-3-yloxy]-acetic acid tert-butyl ester

HRID 1931459
Notes
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Reaction equation

HRID 1931459 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[C:17]([O:21][C:22](=[O:38])[CH2:23]OC1C=NC(C2C=CC=CC=2F)=CC=1)([CH3:20])([CH3:19])[CH3:18].C(OC(=O)CBr)(C)(C)C>CN(C=O)C>[C:17]([O:21][C:22](=[O:38])[CH2:23][O:16][C:13]1[CH:14]=[N:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)([CH3:20])([CH3:19])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 463127886-(4-Fluorophenyl)pyridin-3-OLHCID 68536675[6-(2-Fluoro-phenyl)-pyridin-3-yloxy]-acetic acid tert-butyl ester

Product 1

HCID 68536693[6-(4-Fluoro-phenyl)-pyridin-3-yloxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

119 mg (2.72 mmol) of sodium hydride (55% in mineral oil) were added to 430 mg (2.27 mmol) of 6-(4-fluoro-phenyl)-pyridin-3-ol (prepared analogously as described in Example 76(a) to (d)) in 10 ml of DMF, and the mixture was stirred at room temperature for 60 min. Then 532 mg (2.72 mmol) of bromoacetic acid tert-butyl ester were added, and the reaction mixture was stirred at room temperature for 3 h. After evaporation, water and ethyl acetate were added. The organic phase was separated, dried, and evaporated. Yield: 433 mg.

Workup

  1. customprepared analogously
  2. stirringthe reaction mixture was stirred at room temperature for 3 h
  3. customAfter evaporation, water and ethyl acetate
  4. additionwere added
  5. customThe organic phase was separated
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-fdd0f3aced614d0a8afb922b1ea14767
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188291B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes