7-METHYL-2-(3-NITROPHENYL)IMIDAZO[1,2-A]PYRIDINE synthesis
- Product Name:7-METHYL-2-(3-NITROPHENYL)IMIDAZO[1,2-A]PYRIDINE
- CAS Number:54970-96-6
- Molecular formula:C14H11N3O2
- Molecular Weight:253.26
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Yield:54970-96-6 70%
Reaction Conditions:
with iron(III) chloride in N,N-dimethyl-formamide at 110; for 5 h;
Steps:
7-Methyl-2-(3-nitrophenyl)imidazo[1,2-a]pyridine (5bia)
General procedure: mixture of 2-aminopyridine 1a (94 mg, 1 mmol) and 4-chlorobenzaldehyde 2a (154 mg,1.1 mmol) was heated in presence of anhydrous FeCl3 (20 mol%) in nitromethane 3a (2 mL)and DMF (1 mL) at 110 °C for 5h (TLC). After completion, the reaction mixture was cooledto room temperature and extracted with dichloromethane (10 mL) followed by washing withbrine (5 mL) and dried over Na2SO4. After evaporation of solvent the crude product waspurified by column chromatography on silica gel using petroleum ether/ethylacetate (3:1 to2:1) as eluent. Yellowish white solid. Mp. 138-140 C; Yield: 78%; 1H NMR (400 MHz,CDCl3): δ 8.09 (d, J = 6.8 Hz, 1H), 7.87 (d, J = 8.8 Hz, 2H), 7.81 (s, 1H), 7.61 (d, J = 8.8 Hz,1H), 7.40 (d, J = 8.4 Hz, 2H), 7.19-7.14 (m, 1H), 6.77 (t, J = 6.4 Hz, 1H); 13C NMR (100MHz, CDCl3): δ 145.8, 144.7, 133.8, 132.3, 129.0, 127.3, 125.7, 125.0, 117.6, 112.7, 108.3.
References:
Santra, Sougata;Mitra, Shubhanjan;Bagdi, Avik Kumar;Majee, Adinath;Hajra, Alakananda [Tetrahedron Letters,2014,vol. 55,# 37,p. 5151 - 5155] Location in patent:supporting information
