Adding a certain compound to certain chemical reactions, such as: 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1000342-11-9, category: esters-buliding-blocks
01629] Step 4: Synthesis of methyl 5-bromo-2-methyl-3-[(oxan-4-yl)amino]benzoate[01630] To a solution of methyl 3-amino-5-bromo-2-methylbenzoate (3.0 g, 12 mmol) in 1 ,2- dichloroethane (48 ml) under nitrogen, was added oxan-4-one (2.3 ml, 25 mmol) followed by acetic acid (4.2 ml, 74 mmol). The reaction mixture was stirred for 5 minutes before the addition of sodium triacetoxyborohydride (7.8 g, 37 mmol). After stirring for 64 hours, deionized water (100 ml) was added and the mixture was neutralized with solid NaHC03. The phases were separated and the aqueous layer was extracted with EtOAc (4 x 50 ml). The combined organic extracts were dried over MgS04, filtered and concentrated in-vacuo. The residue was purified by flash column chromatography (50g silica, Isolute cartridge, 10-30% EtOAc:Heptanes) to give the title compound (3.5 g 85%) as a white solid. LC-MS 99.8m/z= 327.9, 328.9, 329.9, 330.9; NMR (500 MHz, Chloroform-d) delta ppm 7.24 (d, J=1.73 Hz, 1 H) 6.85 (d, J=l .58 Hz, 1 H) 4.03 (dt, J=l 1 .82, 3.3 1 Hz, 2 H) 3.88 (s, 3 H) 3.66 (br.s., 1 H) 3.56 (td, J=U .55, 1 .97 Hz, 2 H) 3.47 – 3.55 (m, 1 H) 2.24 (s, 3 H) 2.06 (d, J= 13.56 Hz, 2 H) 1.47 – 1 .60 (m, 2 H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromo-2-methylbenzoate, and friends who are interested can also refer to it.
Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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