Bromine → 2-(4-Amino-5-bromo-2-cyano-3-methylaminophenyl)-2-methyl-3-oxobutyric acid ethyl ester

HRID 1634238Notes

Reaction equation

HRID 1634238 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:17][CH3:18])[C:11]=1[C:19]#[N:20])([CH3:9])[C:6](=[O:8])[CH3:7])[CH3:2].[Br:22]Br>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:10]1[CH:15]=[C:14]([Br:22])[C:13]([NH2:16])=[C:12]([NH:17][CH3:18])[C:11]=1[C:19]#[N:20])([CH3:9])[C:6](=[O:8])[CH3:7])[CH3:2]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 110661612-(4-Amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester

Product 1

HCID 118247542-(4-Amino-5-bromo-2-cyano-3-methylaminophenyl)-2-methyl-3-oxobutyric acid ethyl esterYield 53%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-amino-2-cyano-3-methylaminophenyl)-2-methyl-3-oxobutyric acid ethyl ester from Example 4 (9.02 g, 31.2 mmol) in CHCl3 (90 mL) was added bromine (4.98 g, 31.2 mmol) dropwise at ambient temperature. After the addition of bromine, the reaction mixture was diluted with ethyl acetate (800 mL). This solution was washed successively with sat. NaHCO3 solution and brine and dried. The residue after evaporation was purified by flash chromatography in hexanes/EtOAc 2:1 to yield 2-(4-amino-5-bromo-2-cyano-3-methylaminophenyl)-2-methyl-3-oxobutyric acid ethyl ester as an oil (6.06 g, 53%).

Workup

  1. washThis solution was washed successively with sat. NaHCO3 solution and brine
  2. customdried
  3. customThe residue after evaporation
  4. customwas purified by flash chromatography in hexanes/EtOAc 2:1

Sources & evidence

ORD record
ord-4d35ad7a8ebd43c88942ec12917ad2ee
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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