5-Bromo-2-chloronicotinic acid synthesis
- Product Name:5-Bromo-2-chloronicotinic acid
- CAS Number:29241-65-4
- Molecular formula:C6H3BrClNO2
- Molecular Weight:236.45
104612-36-4
29241-65-4
Step B. Synthesis of 5-bromo-2-chloronicotinic acid. A mixture of 5-bromo-2-hydroxynicotinic acid (32.9 g, 0.151 mol), dichlorosulfoxide (167 mL), and N,N-dimethylformamide (10.5 mL) was heated to reflux for 4 hours at 70°C. The reaction was carried out with the addition of water. Upon completion of the reaction, the mixture was concentrated, cooled to 0°C, and the reaction was quenched by the slow addition of water to give an off-white precipitate. The precipitate was stirred in water for 1 h and subsequently collected by filtration and dried under vacuum to give 5-bromo-2-chloronicotinic acid (35.5 g, 99% yield). The product can be used directly in the subsequent reaction without further purification or can be purified by recrystallization in hot water. Mass spectrum (electrospray ionization): calculated value C6H3BrClNO2, 234.90; measured value m/z, 236.2 [M + H]+. 1H NMR (acetone-d6): δ 8.66 (d, J = 2.5 Hz, 1H), 8.43 (d, J = 2.5 Hz, 1H).
104612-36-4
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29241-65-4
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Yield:29241-65-4 99%
Reaction Conditions:
Stage #1:5-bromo-2-hydroxynicotinic acid with thionyl chloride in N,N-dimethyl-formamide at 70; for 4 h;
Stage #2: with water in N,N-dimethyl-formamide for 1 h;
Steps:
48.B 8-(4-Methoxy-phenyl)-6-methyl-3-(4-piperidin-1-yl-but-1-ynyl)-5,6,7,8-tetrahydro-[1,6]naphthyridine trifluoroacetic acid salt
Step B. 5-Bromo-2-chloro-nicotinic acid. A mixture of 5-bromo-2-hydroxy-nictonic acid (32.9 g, 0.151 mol), SOCl2 (167 mL), and DMF (10.5 mL) was heated at 70° C. for 4 h. The mixture was concentrated, cooled to 0° C., and quenched slowly with H2O to give an off-white precipitate. The precipitate was stirred in H2O for 1 h, and then was collected by filtration and dried under vacuum to give the title compound (35.5 g, 99%). The product was carried on to the next step without purification, but alternatively may be recrystallized from hot H2O. MS (ESI): mass calcd. for C6H3BrClNO2, 234.90; m/z found, 236.2 [M+H]+. 1H NMR (acetone-d6): 8.66 (d, J=2.5, 1H), 8.43 (d, J=2.5, 1H).
References:
Carruthers, Nicholas I.;Keith, John M.;Letavic, Michael A.;Shah, Chandravadan R. US2006/287292, 2006, A1 Location in patent:Page/Page column 26
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29241-65-4
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