2-Methyl-3-nitropyridine

Uses

2-Methyl-3-nitropyridine is used as a starting reagent to synthesize 3-substituted-4 or 6-azaindoles, and is also used as a reagent to prepare 3-azaindolyl-4-arylmalemides (compounds that exhibit antiproliferative activity).

Reactions

2-Methyl-3-nitropyridine could be used to synthesize dichloro-(3-nitro-2-pyridyl)methylphosphonic dichloride. The chlorination of 2-methyl-3-nitropyridine using a mixture of PCl5 in POCl3[1].

Synthesis Reference(s)

Tetrahedron, 54, p. 6311, 1998 DOI: 10.1016/S0040-4020(98)00328-7
Journal of Heterocyclic Chemistry, 29, p. 359, 1992 DOI: 10.1002/jhet.5570290213
Synthetic Communications, 20, p. 2965, 1990 DOI: 10.1080/00397919008051513

Synthesis

Suzuki Reaction. A mixture of 2-chloro-3-nitro-pyridine 1 (793 mg, 5 mmol), methylboronic acid (329 mg, 5.5 mmol), Pd(PPh3) 4 (578 mg, 0.5 mmol) and K2CO 3 (2.073 g, 15 retool) in dioxane (25 mL) was refluxed for 2 days, then cooled to room temperature and filtered. The solvent was removed and the residue was isolated by chromatography (hexanes-EtOAc = 1:1) to provide 623 mg (90%) of 2-methyl-3-nitropyridine[2].

References

[1] Amrane D, et al. "Dichloro{4-(4-chlorophenoxy)phthalazin-1-yl} methylphosphonic dichloride." Molbank (2022).
[2] Niu, Chuansheng , et al. "Synthesis of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP)." 54.23(1998):6311-6318.