Electric Literature of 6271-78-9 ,Some common heterocyclic compound, 6271-78-9, molecular formula is C6H5ClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 1-6 6-chloro-N-(7-chloro-2-(oxazol-2-yl)-4-oxo-1-phenyl-1,4-dihydroquinolin-3-ylmethyl)nicotin-amide A 5 mL round-bottomed flask was charged with 6-chloronicotinamide (14 mg, 0.091 mmol), sodium hydride (60% suspension in mineral oil, 5.0 mg, 0.013 mmol) and DMF (1 mL) to give a slightly white suspension. This mixture was stirred at 50 C for 15 min. During this time, the reaction mixture became more cloudy and difficult to stir. The reaction mixture was cooled to room temperature. A solution of 3-(bromomethyl)-7- chloro-2-(oxazol-2-yl)-l-phenylquinolin-4(lH)-one (38 mg, 0.091 mmol) in DMF (1 mL) was added dropwise to the room temperature reaction mixture. The reaction was stirred at 50 C over 1 hr. LC/MS at this time suggested formation of the desired product. The reaction mixture was allowed to cool gradually to room temperature, then it was stirred at room temperature overnight. The reaction was quenched via addition of 1 mL water slowly. The quenched reaction mixture was then partitioned between 20 mL ethyl acetate and 20 mL water. The organic phase was dried (MgS04), filtered, then concentrated over silica gel. The silica gel supported crude product was loaded onto a 40 gram silica gel column. Flash chromatography (75% ethyl acetate-hexanes ramped to 100% ethyl acetate) was used to partially purify the desired product 6-chloro-N-(7-chloro-2-(oxazol- 2-yl)-4-oxo- 1 -phenyl- 1 ,4-dihydroquinolin-3-ylmethyl)nicotinamide from the side product 6-chloro-N,N-bis((7-chloro-2-(oxazol-2-yl)-4-oxo-l -phenyl- l,4-dihydroquinolin-3- yl)methyl)nicotinamide. Homogeneous fractions were concentrated to provide 6-chloro- N-(7-chloro-2-(oxazol-2-yl)-4-oxo-l -phenyl- l,4-dihydroquinolin-3-ylmethyl)nicotin- amide as 1 mg (2% yield) of a white solid. 1H NMR (chloroform-d) delta ppm 8.75 (d, 7=2.4 Hz, 1 H) 8.42 (d, 7=8.6 Hz, 1 H) 7.99 (dd, 7=8.2, 2.7 Hz, 1 H) 7.68 (bs, 1 H), 7.58 (s, 1 H), 7.45 (m, 3 H), 7.39 (dd, 7=8.5, 2.0 Hz, 1 H) 7.34 (d, 7=8.2 Hz, 1 H) 7.28 (m, 2H) 7.13 (s, 1H) 6.85 (d, J=2.0 Hz, 1 H) 4.47 (d, 7=5.5 Hz, 2 H). MS calcd. for C25H16C12N4O3
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6271-78-9, 6-Chloropyridine-3-carboxamide, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BILOTTA, Joseph Anthony; CHEUNG, Adrian Wai-Hing; FIROOZNIA, Fariborz; GUERTIN, Kevin Richard; HAYDEN, Stuart; HAYNES, Nancy-Ellen; LUKACS-LESBURG, Christine M.; MARCOPULOS, Nicholas; MERTZ, Eric; QI, Lida; QIAN, Yimin; SO, Sung-Sau; TAN, Jenny; THAKKAR, Kshitij Chhabilbhai; WO2013/7676; (2013); A1;,
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