Methyl6-bromo-2-(methylamino)nicotinate synthesis
- Product Name:Methyl6-bromo-2-(methylamino)nicotinate
- CAS Number:1034131-15-1
- Molecular formula:C8H9BrN2O2
- Molecular Weight:245.0733
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Yield:-
Reaction Conditions:
Stage #1: methyl 6-methoxy-2-methylaminopyridine-3-carboxylatewith phosphorus(V) oxybromide;phosphoric acid;Pyridine hydrobromide in benzene;Heating / reflux;
Stage #2: with sodium carbonate in water;benzene; pH=7 - 8;
Steps:
11.d
(d) Methyl 6-bromo-2-(methylamino)nicotinate. A mixture of methyl 6-methoxy-2-(methylamino)nicotinate (20 g, 100 mmol), POBr3 (58.6 g, 204.4 mmol), H3PO4 (1.0 g, 10.2 mmol) and C5H5N-HBr (1.6 g, 10.0 mmol) in benzene (200 mL) was heated at reflux overnight. The reaction mixture was left to reach room temperature, poured into ice-water, basified to pH = 7-8 with sodium carbonate, and extracted with DCM. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, and filtered. The filtrate was evaporated under reduced pressure, and the residue purified by silica gel chromatography to give the title compound.
References:
WO2008/76425,2008,A1 Location in patent:Page/Page column 43
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