N-bromobutanimide → 5-Bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

HRID 1845881Notes

Reaction equation

HRID 1845881 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:11].C1C(=O)N([Br:27])C(=O)C1>C(#N)C>[Br:27][C:17]1[CH:18]=[C:13]([O:12][CH:10]([C:3]2[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[Cl:1])[CH3:11])[C:14]([NH2:19])=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 211113963-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

Product 1

HCID 211114785-Bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amineYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-aminopyridine (24.0 g, 79.9 mmol) was dissolved in acetonitrile (250 mL), and to which was added NBS (14.2 g, 79.9 mmol) under the cooling of ice bath. After 15 min, the solvent in the resultant mixture was evaporated under reduced pressure, and then purified via silica gel column chromatography (petroleum ether:ethyl acetate=3:1) to yield the target product as solid powder of soil colour (23.2 g, 61.1 mmol; yield=76%).

Workup

  1. temperaturecooling of ice bath
  2. customthe solvent in the resultant mixture was evaporated under reduced pressure
  3. custompurified via silica gel column chromatography (petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-46058fce9a5c48a19538bea8404824e7
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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