1,2-Dichloroethane → 5-Bromo-N-methylpyridine-2-carboxamide

HRID 2261226Notes

Reaction equation

HRID 2261226 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:24][C:22]=2C=1>CN(C=O)C.O.CCN(CC)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:24][CH3:22])=[O:10])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 6085445-Bromopyridine-2-carboxylic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 228316205-Bromo-N-methylpyridine-2-carboxamideYield 50.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

5-Bromo-2-pyridinecarboxylic acid (D10) (1 g) was dissolved in dry DMF (50 ml) and treated with methylamine hydrochloride (0.42 g), EDC (1.29), HOBT (0.56 g) and Et3N (2.4 ml). The reaction was stirred at rt overnight then poured into water (200 ml) and extracted with DCM (50 ml). The organic extract was washed with brine (5×50 ml), dried (magnesium sulfate) and evaporated to give the title compound (D11) as a yellow crystalline solid (0.45 g). LCMS electrospray (+ve) 349 (MH+).

Workup

  1. extractionextracted with DCM (50 ml)
  2. extractionThe organic extract
  3. washwas washed with brine (5×50 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-176d30156a454c06bb2be00faa5993c1
Source dataset
uspto-grants-2010_12
Patent number
US07846922B2

Reaction notes

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