1-Butanol → 6-Bromo-(4-methoxybenzylamino)pyridine

HRID 2187395Notes

Reaction equation

HRID 2187395 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.C(O)CCC>CCOC(C)=O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:16][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 122742,6-DibromopyridineHCID 754524-Methoxybenzylamine

Product 1

HCID 234355096-Bromo-(4-methoxybenzylamino)pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,6-dibromopyridine 16-1 (15 g, 70 mmol), 4-methoxybenzylamine (25 mL, 191 mmol) and butanol (25 mL) was heated at 100° C. for 6 days. After cooling, EtOAc was added, the solids removed by filtration and the solution concentrated in vacuo. Purification of the residue by silica gel chromatography (Hexane:EtOAc 4:1) afforded the title compound 16-2 as a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe solids removed by filtration
  3. concentrationthe solution concentrated in vacuo
  4. customPurification of the residue by silica gel chromatography (Hexane:EtOAc 4:1)

Sources & evidence

ORD record
ord-557539c57299493bae34e426a08b01e5
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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