Electric Literature of 76153-06-5, These common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, 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.
EXAMPLE 375-Methyl-7-r3-(piperidin-l-ylmethyl)phenyl]quinoxalineGlyoxal (10 drops of a 40% solution in water) was added to a solution of 5- bromo-2,3-diaminomethylbenzene (80 mg, 0.4 mmol) in ethanol (3 mL). The mixture was stirred and left to stand at r.t. for 1 h. The mixture was partitioned between water and EtOAc (20 mL each), and the organic phase was dried (MgSO4) and concentrated in vacuo. The residue was dissolved in DME (1.2 mL), and 3-(piperidin-l-ylmethyl)phenyl- boronic acid pinacol ester hydrochloride (135 mg, 0.4 mmol), 2M aqueous sodium carbonate solution (0.6 mL, 0.9 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) were added. The mixture was heated to 1200C in a sealed tube, under microwave irradiation, for 20 minutes. The mixture was partitioned between water and EtOAc (2 mL each), and the organic phase was concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (5 mg, 4% over the two steps) as a pale yellow-brown gum. delta? (CDCl3) 8.87 (d, IH), 8.85 (d, IH), 8.17 (s, IH), 7.93 (s, IH), 7.72 (s, IH), 7.65 (d, IH), 7.46 (t, IH), 7.39 (d, IH), 3.58 (s, 2H), 2.88 (s, 3H), 2.34-2.52 (m, 4H), 1.51-1.68 (m, 4H), 1.39-1.51 (m, 2H). LCMS (ES+) 318 (M+H)+, RT 2.43 minutes.
Statistics shows that 5-Bromo-3-methylbenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 76153-06-5.
Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
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