Introduction of a new synthetic route about 6-Chloro-4-methylnicotinaldehyde

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-38-9, its application will become more common.

Reference of 884495-38-9 ,Some common heterocyclic compound, 884495-38-9, molecular formula is C7H6ClNO, 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.

General procedure: To a solution of Intermediate 15B (0.50 g, 4.46 mmol) and 6bromo4methoxynicotinonitrile (0.95 g, 4.46 mmol) in dioxane (20 mL) was added K2CO3 (1.54 g, 11.15 mmol) and XANTPHOS (0.52 g, 0.89 mmol) and the resulting reaction mixture was degassed with nitrogen for 5 minutes. Pd2(dba)3(0.41 g, 0.45 mmol) was added and the resulting mixture was degassed again for 5 minutes then heated at 100 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2 2.5 % MeOH in DCM), to obtain Intermediate 15C (0.40 g, 36.70%) as a pale yellow solid.1H NMR (400 MHz, DMSOd6) G ppm 2.65 (t, J = 6.78 Hz, 2 H), 3.61 (td, J = 6.78, 5.02 Hz, 2 H), 4.10 (s, 3 H), 4.62 4.76 (m, 1 H), 7.58 (s, 1 H), 7.81 (s, 1 H), 8.47 (s, 1 H), 8.73 (s, 1 H). LCMS (MethodI): retention time 0.83 min, [M+H] 245.3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-38-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
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