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

HRID 1931380Notes

Reaction equation

HRID 1931380 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][OH:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[C:13]1[N:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])=[CH:17][CH:18]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:9])[CH2:7][O:8][C:13]1[N:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])=[CH:17][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11815394Tert-butyl 2-hydroxyacetateHCID 457878323-Bromo-6-(2-fluoro-phenyl)-pyridazine

Product 1

HCID 68537532[6-(2-Fluoro-phenyl)-pyridazin-3-yloxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

37.6 mg (0.285 mmol) of hydroxyacetic acid tert-butyl ester were dissolved in 10 ml of DMF, 12.4 mg of sodium hydride (55% in mineral oil) were added, and the mixture was stirred at room temperature for 15 min. Then 60 mg (0.237 mmol) of 3-bromo-6-(2-fluoro-phenyl)-pyridazine in 2 ml of DMF were added, and the reaction mixture was stirred at 60° C. for 5 h and at 120° C. for 5 h. After evaporation to dryness, the crude product was directly employed in the subsequent step.

Workup

  1. stirringthe reaction mixture was stirred at 60° C. for 5 h and at 120° C. for 5 h
  2. customAfter evaporation to dryness

Sources & evidence

ORD record
ord-975cba7e3a554797be2f11c606eda0ca
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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