Electric Literature of 1245643-11-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a solution of a mixture of intermediates 3a and 3b (75/25 evaluated by LC/MS) (195g, 554 mmol) in DMSO (2000 mL) was added vinylbutylether (166 g, 1661. mmol) and tri- ethyl amine (400 mL, 2768 mmol, 0.7g/mL) under N2atmosphere. Pd(OAc)2(12.4g, 55mmol) and DPPP (45.6g, 11 lmmol) were added. The mixture was purged again with N2and heated to 100 C overnight. After cooling down to room temperature, HCl (3M, 1845mL, 5536 mmol) was added portionwise under ice batch and the mixture was stirred for 1 hour. The pH of the mixture was adjusted to 8 with NaHC03. The mixture was filtered. The cake was washed with ethyl acetate (1000 mL), then dissolved in CH2C12(1500 mL*2) and filtered. The filtrate was washed with brine (500 mL), evaporated to give a crude yellow solid (200 g) mainly containing intermediate 8a. This residue was purified by silica gel chromatography (eluent: ethyl acetate= 100%). The desired fractions were collected and the solvent was concentrated to dryness under vacuum to give 100 g (57%>) of intermediate 8a as yellow solid.Alternatively, the previous reaction was also carried out using EtOH as solvent at a temperature of 70C.
The synthetic route of Methyl 3,4-diamino-5-bromobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
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