6-CHLORO-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE

General procedure: A vial containing a mixture of 2-aminopyridine (1) (1 mmol), and α-bromoketone (2) (1 mmol) was placed in a microwave synthesiser. The vial was subjected to microwave irradiation programmed at 65 °C, 120 W and 1 bar pressure. After 15–20 min of irradiation, the mixture was cooled to room temperature. The crude product (3) was subjected to column chromatography on alumina (solvent: dichloromethane) to obtain the pure products.General procedure: To a solution of 2-aminopyridine (1 equiv.) in acetone was added the appropriate α-bromoketone (1 equiv.). The solution was stirred at 25 °C with reaction times ranging from 2 to 6 hours. After completion of the reaction (monitored by LC-MS), the formed precipitate was filtered off and washed with acetone (15 mL). The solid was neutralized with a saturated NaHCOGeneral procedure: Initially, 2-amino pyridine (0.25 mmol), substituted acetophenones (0.25 mmol), iodine(20 molpercent, 13 mg), and cyclohexane (2 mL) were taken in 25-mL round-bottomed flaskand stirred at 60 °C. The stirring was continued for 15 min under this condition. Later, the reaction mixture diluted with 30 mL of water and collected the organic layer with ethylacetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure.The crude product was purified through column chromatography using petroleumether and ethyl acetate as an eluant.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 molpercent) 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: 78percent; 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.

Molecular Weight:228.67
XLogP3:4.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:228.0454260
Monoisotopic Mass:228.0454260
Topological Polar Surface Area:17.3
Heavy Atom Count:16
Complexity:240
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes