HCID 86623751, compound → HCID 66998716, compound

HRID 1161816Notes

Reaction equation

HRID 1161816 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[F:22])=[CH:12][C:11]([N:24]=[N+]=[N-])([Cl:23])[NH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Zn].C(OCC)(=O)C>[C:1]([O:5][C:6]([C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[F:22])=[CH:12][C:11]([NH2:24])([Cl:23])[NH:10][N:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86623751HCID 86623751, compound

Product 1

HCID 66998716HCID 66998716, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the stirred solution of 6-azido-4-(4-bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester (122 mg, 0.30 mmol) in 5 ml of mixed solvents (3:1 v/v, dichloromethane/acetic acid) is added zinc powder (98 mg, 1.5 mmol) at room temperature. After three hours, the reaction mixture is poured into ethyl acetate (50 μl). The organic layer is washed with water, saturated NaHCO3 (30 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. washThe organic layer is washed with water, saturated NaHCO3 (30 ml×3) and saturated NaCl (30 ml×3)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-f1a656354b8f4cbb93484056a715f285
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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