Sodium hydride → (6-Bromo-pyridazin-3-yloxy)-acetic acid tert-butyl ester

HRID 1931383Notes

Reaction equation

HRID 1931383 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][OH:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:12][C:13]1[N:14]=[N:15][C:16](Br)=[CH:17][CH:18]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:9])[CH2:7][O:8][C:16]1[N:15]=[N:14][C:13]([Br:12])=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2488523,6-DibromopyridazineHCID 11815394Tert-butyl 2-hydroxyacetate

Product 1

HCID 86638119(6-Bromo-pyridazin-3-yloxy)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

277.8 mg (2.1 mmol) of hydroxyacetic acid tert-butyl ester and 100.9 mg of sodium hydride (55% in mineral oil) in 15 ml of DMF were stirred at room temperature for 30 min. Then 500 mg (2.1 mmol) of 3,6-dibromopyridazine were added, and the reaction mixture was stirred at 60° C. for 2 h. After evaporation to dryness, the residue was stirred with ethyl acetate, the solution filtered, evaporated, and the crude product (450 mg) directly employed in the subsequent step.

Workup

  1. customAfter evaporation to dryness
  2. stirringthe residue was stirred with ethyl acetate
  3. filtrationthe solution filtered
  4. customevaporated

Sources & evidence

ORD record
ord-caef1ec6fadf466eb1b44077cf0233c9
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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