METHYL 3-BROMOMETHYLPYRIDINE-2-CARBOXYLATE synthesis
- Product Name:METHYL 3-BROMOMETHYLPYRIDINE-2-CARBOXYLATE
- CAS Number:116986-09-5
- Molecular formula:C8H8BrNO2
- Molecular Weight:230.06
59718-84-2
116986-09-5
General procedure for the synthesis of methyl 3-(bromomethyl)pyridine-2-carboxylate from methyl 3-methylpyridine-2-carboxylate: methyl 3-methylpyridine-2-carboxylate (4.1 g, 27.1 mmol), N-bromosuccinimide (NBS, 5.8 g, 32.5 mmol) and azobisisobutyronitrile (AIBN, 100 mg, 0.61 mmol) were dissolved in carbon tetrachloride (55 mL). The reaction mixture was stirred at 90 °C for 16 h under nitrogen protection. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The concentrate was purified by column chromatography to afford the target product methyl 3-(bromomethyl)pyridine-2-carboxylate (5.0 g, 80.6% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.67 (dd, J = 1.6, 4.6 Hz, 1H), 7.91 (dd, J = 1.5, 7.9 Hz, 1H), 7.48 (dd, J = 4.6, 7.9 Hz, 1H), 4.95 (s, 2H), 4.07-4.03 (m, 3H). lCMS ( m/z): 229.9 ([M + H]+).
59718-84-2
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$8.00/1g
116986-09-5
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$45.00/10mg
Yield: 80.6%
Reaction Conditions:
with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane at 90; for 16 h;Inert atmosphere;
Steps:
7.2 methyl 3-(bromomethyl)picolinate
A mixture of methyl 3-methylpicolinate (4.1 g, 27.1 mmol), NBS (5.8 g, 32.5 mmol), and AIBN (100 mg, 0.61 mmol) in carbon tetrachloride (55 mL) was stuffed at 90 °C for 16 h under nitrogen. The mixture was filtered and concentrated before being purified by column chromatography to give the desired product (5.0 g, 80.6%). ‘H NMR (400 MHz, CDC13, ): 8.67 (dd, J= 1.6, 4.6 Hz, 1 H), 7.91 (dd, J= 1.5, 7.9 Hz, 1 H), 7.48 (dd, J= 4.6, 7.9 Hz, 1 H), 4.95 (s, 2 H), 4.07 - 4.03 (m, 3 H). LCMS (mlz): 229.9 (M+1).
References:
EPIZYME, INC.;DUNCAN, Kenneth, W.;CHESWORTH, Richard;MUNCHHOF, Michael, John;SHAPIRO, Gideon WO2015/200677, 2015, A2 Location in patent:Paragraph 00472; 00473
3430-17-9
454 suppliers
$4.00/5g
116986-09-5
61 suppliers
$45.00/10mg