1,2-Dichloroethane → 5-Bromo-N-methylpyridine-2-carboxamide
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]=1Participants
8
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 (1.2 g), 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
- extractionextracted with DCM (50 ml)
- extractionThe organic extract
- washwas washed with brine (5×50 ml)
- dry with materialdried (magnesium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-951e4bbe6dca4b4d9a1b69c725d0796c
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492375B2
Reaction notes
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