Extracurricular laboratory: Synthetic route of 884495-39-0

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. 884495-39-0, 5-Bromo-2-methoxypyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference of 884495-39-0 ,Some common heterocyclic compound, 884495-39-0, molecular formula is C6H7BrN2O, 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.

To 5-bromo-2-(methyloxy)-3-pyridinamine (18.93 g, 93 mmol, available from Asymchem) in a 1 L round-bottom flask was added nitrogen-purged 1 ,4-Dioxane (500 ml.) followed by 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1 ,3,2-dioxaborolane (47.4 g, 186 mmol), potassium acetate (27.5 g, 280 mmol) (0.402 g, 0.493 mmol) and PdCI2(dppf)-CH2CI2 adduct (7.61 g, 9.32 mmol). The mixture was then stirred at 8O0C under nitrogen. The reaction mixture was allowed to cool then partitioned between ethyl acetate and water. The mixture was filtered through a celite pad and the aqueous layer extracted further with ethyl acetate (2X). The combined organics were washed with water, brine and dried over magnesium sulphate overnight. The residue was purified on 1.5Kg Silica cartridge, eluting a 0-50% ethyl acetate/dichloromethane over 10 column volumes. The appropriate fractions were combined and evaporated to dryness. The residue was triturated with cyclohexane, the solid filtered off and dried in vacuo to leave the title compound as a light pink solid (1.1 g). LCMS (Method A) Rt 0.91 mins, MH+ 251A second crop was obtained from the above filtrate and after drying gave a further portion of the title compound as a light pink solid (2.95g).

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. 884495-39-0, 5-Bromo-2-methoxypyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; HAMBLIN, Julie, Nicole; HARRISON, Zoe, Alicia; JONES, Paul, Spencer; KEELING, Suzanne, Elaine; LE, Joelle; LUNNISS, Christopher, James; PARR, Nigel, James; WO2010/102958; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem