Chlorosuccinimide → HCID 66617807, compound

HRID 911015Notes

Reaction equation

HRID 911015 reaction equation
[Br:1][C:2]1[C:3]([O:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:18]N1C(=O)CCC1=O>C(#N)C>[Br:1][C:2]1[C:3]([O:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[C:4]([Cl:18])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 66617813HCID 66617813, compound

Product 1

HCID 66617807HCID 66617807, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-4-(2,6-difluorophenoxy)pyridin-2-amine (301 mg, 1.0 mmol) and N-chlorosuccinimide (1.1 mmols) in acetonitrile (50 mL) is stirred at room temperature for one hour then heated at reflux for 24 hours. The reaction mixture is cooled and concentrated. The residue is purified via column chromatography to afford 5-bromo-3-chloro-4-(2,6-difluorophenoxy)pyridin-2-amine.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated
  5. customThe residue is purified via column chromatography

Sources & evidence

ORD record
ord-3eb51859f6c14f61a2a64d4764aa37e5
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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