2,6-Dibromopyridine → 6-Bromo-N-[(4-chlorophenyl)methyl]-2-pyridinamine

HRID 1886834Notes

Reaction equation

HRID 1886834 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[N:12]=1>C(OCC)C>[Br:10][C:11]1[N:12]=[C:13]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 122742,6-DibromopyridineHCID 660364-Chlorobenzylamine

Product 1

HCID 575979386-Bromo-N-[(4-chlorophenyl)methyl]-2-pyridinamineYield 100.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial was charged with 4-chloro benzylamine (700 mg; 5 mmol; 5 equivalents) and 2,6-dibromo pyridine (238 mg, 1 mmol). The reaction mixture was stirred in the microwave at 150° C. for three times ten minutes (200 W maximum). The reaction mixture was diluted with diethyl ether (50 ml), washed with 10% aqueous citric acid, saturated aqueous sodium bicarbonate and brine. The organic was dried over magnesium sulfate and, after filtration, concentrated in vacuo to afford an oil as the title compound (300 mg, 100% yield). LC/MS: 299 [M+H]

Workup

  1. washwashed with 10% aqueous citric acid, saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe organic was dried over magnesium sulfate
  3. filtrationafter filtration
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-988a89491e13474498cef932fd0dafff
Source dataset
uspto-grants-2013_08
Patent number
US08501446B2

Reaction notes

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