Methylamine → 6-bromo-N-methylpyridin-2-amine

HRID 2079752Notes

Reaction equation

HRID 2079752 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[N:5]=1>O1CCCC1>[CH3:6][CH2:7][CH2:8][CH:9]([CH3:4])[CH3:1].[Br:3][C:4]1[N:5]=[C:6]([NH:2][CH3:1])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 122742,6-Dibromopyridine

Product 2

HCID 78922-MethylpentaneHCID 134703156-bromo-N-methylpyridin-2-amineYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a 2; M solution of methylamine in tetrahydrofuran (33.6; mL, 67.12; mmol) to 2,6-dibromopyridine (5.3; g, 22.37; mmol) and heat overnight at 110° C. in a sealed tube. Concentrate and purify by silica gel chromatography, gradient eluting from 0:100; to 20:80; ethyl acetate:iso-hexane to give the title compound (0.345; g, 8%) as a pale yellow oil which crystallizes on standing. MS (m/z): 185,187; (M+1).

Workup

  1. additionAdd a 2
  2. concentrationConcentrate
  3. custompurify by silica gel chromatography
  4. washgradient eluting from 0:100

Sources & evidence

ORD record
ord-9503b15aa0e24498bb8d08a1e32cf210
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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