These common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, 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. Formula: C9H10BrNO2
Example 18:Methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoateTo a solution of the compound of example 17 (15 g, 61.5 mmol) in DOE (100 ml) were added dihydro-2H-pyran-4(3H)-one (11.35 mL, 123 mmol) and acetic acid (21 .11 mL, 369 mmol) and stirred at RT for 2h. The reaction mass was cooled to 0 00 and sodium triacetoxyborohydride (39.1 g, 184 mmol), was addedlot wise in 1 h which was left to stir at RT for 16h. After completion of the reaction, water was added and extracted with ethyl acetate. The compound was adsorbed on silica and purified by column chromatography (silica gel, 10-80 % ethyl acetate in petroleum ether) to yield the title compound.Yield: 15.1 g (73.6 %); 1H NMR (DMSO-d6, 300 MHz): 66.97-6.93 (m, 2H),3.87-3.85 (m, 2H), 3.80 (5, 3H), 3.59-3.55 (m, 1H), 3.46-3.41 (m, 2H), 2.14 (5,3H), 1.84-1.82 (m, 2H), 1.56-1.53 (m, 2H);MS (ESl+): m/z 329.1 [M+H] HPLO Purity: 98.3 %.
The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GUPTE, Amol; KANDRE, Shivaji; GADEKAR, Pradip, Keshavrao; CHAVAN, Sambhaji; JADHAV, Ravindra, Dnyandev; THAKRE, Gajanan, Amrutrao; BAJAJ, Komal; JANRAO, Ravindra, Ashok; DEHADE, Amol; GAIKWAD, Nitin; KADAM, Kishorkumar; MORE, Tulsidas, Sitaram; GUHA, Tandra; SEELABOYINA, Balapadmasree; SABLE, Vikas, Vasant; WO2015/110999; (2015); A1;,
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