Sodium Azide → 6-Azido-4-(4-Bromo-2-fluoro-phenylamino)-pyridazine-3-carboxylic acid tert-butyl ester

HRID 1161815Notes

Reaction equation

HRID 1161815 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:24]=[N+:25]=[N-:26])=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 595194124-(4-Bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester

Product 1

HCID 595194566-Azido-4-(4-Bromo-2-fluoro-phenylamino)-pyridazine-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester (300 mg, 0.74 mmol) in DMF (5 ml) under argon at room temperature is added sodium azide (96 mg, 1.48 mmol) with stirring. The reaction mixture is stirred at 50° C. for 6 hours. After cooling to room temperature, the reaction mixture is diluted with ethyl acetate and washed with water, saturated NaHCO3 (20 ml×3) and saturated NaCl (30 ml×3). The organic layer is dried over Na2SO4 and concentrated. The residue is purified by flash column chromatography to provide the desired product.

Workup

  1. stirringThe reaction mixture is stirred at 50° C. for 6 hours
  2. washwashed with water, saturated NaHCO3 (20 ml×3) and saturated NaCl (30 ml×3)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-9ec6ae71265b4fc2b6647b32dd817c07
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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