Ethanol → 5-bromo-3-fluoro-N-methylpyridin-2-amine

HRID 445695Notes

Reaction equation

HRID 445695 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5](F)=[N:6][CH:7]=1.[CH3:10][NH2:11].CCO>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([NH:11][CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 145496545-Bromo-2,3-difluoropyridine

Product 1

HCID 596130165-bromo-3-fluoro-N-methylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2,3-difluoropyridine (Matrix, Columbia, USA, 2.53 mmol) and 8 M methylamine in EtOH (Aldrich, Buchs, Switzerland, 2 ml, 16 mmol) was sealed in a vial and heated with microwave irradiation at 100° C. for 30 min. The cooled RM was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title product as an off-white solid. (HPLC: tR 1.94 min (Method A); M+H=205, 207, M−H=203, 205 MS-ES)

Workup

  1. customwas sealed in a vial and
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-a715df92ded24151938856dd69321870
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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