Water → 5-Bromo-N-methylpyridin-2-amine

HRID 558525Notes

Reaction equation

HRID 558525 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[CH3:9][NH2:10].O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 156456635-Bromo-N-methylpyridin-2-amineYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-2-fluoropyridine (2.5 g, 14 mmol) in THF (50 mL) was stirred with a solution of methylamine in THF (c=2 mol/L) (35 mL, 70 mmol) at 23° C. for 16 h. Water was added and the mixture was extracted with ether, the organic layer was dried over Na2SO4. Removal of the solvent in vacuum left a residue which was purified by silica gel column chromatography with heptane/ether, followed by trituration with heptane to give the title compound as a white solid (630 mg, 24%). MS (ISP) 187.1 [(M+H)+], 189.2 [(M+2+H)+].

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customRemoval of the solvent in vacuum
  4. waitleft a residue which
  5. customwas purified by silica gel column chromatography with heptane/ether

Sources & evidence

ORD record
ord-8411ceeb72dc4c4789e98bffff5b9700
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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