Some tips on 91348-45-7

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.91348-45-7,Ethyl 3-bromo-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

91348-45-7, Intermediate 22a : Ethyl 3-bromo-1 -{[4′-(methoxycarbonyl)-4- methylbiphenyl-3-yl]methyl}-1 H-indole-2-carboxylateTo 68.3 g (0.266 mol) of methyl 3′-(hydroxymethyl)-4′-methylbiphenyl- 4-carboxylate in 1.0 L EtOAc was added at 100C 20.5 ml_ (0.280 mol) SOCI2 and 1 ml_ pyridine. The solution was then stirred at room temperature for 12 hrs then washed with 500 ml_ 1.0 N HCI (aq), 500 ml_ sat. NaHCO3 (aq) and 500 ml_ brine then dried over Na2SO4 and concentrated. To 750 mg (2.71 mmol) of this residue was added 660mg (2.46 mmol) of ethyl 3-bromo-1 H- indole-2-carboxylate in 8 ml_ DMF followed by 850 mg (6.16 mmol) K2CO3 and the mixture stirred at 7O0C for 4 hrs. The solution was cooled and 100 ml_ EtOAc was added. The solution was washed with three 25 ml_ portions of H2O and 25 ml_ brine then dried over Na2SO4, concentrated, and purified by silica gel chromatography (120 grams of silica gel eluting with 0-20% EtOAc in hexanes over 45 minutes) to give 1.02 g (82%) of ethyl 3-bromo-1 -{[4′- (methoxycarbonyl)-4-methylbiphenyl-3-yl]methyl}-1H-indole-2-carboxylate as white solid: 1 H NMR (400 MHz, CDCI3). delta 7.93 (d, 2H, J = 8.5 Hz), 7.74 (d, 1 H, J = 7.9 Hz), 7.40-7.22 (m, 7H), 6.54 (s, 1 H), 5.79 (s, 2H), 4.34 (q, 2H, J = 7.4 Hz), 3.87 (s, 3H), 2.46 (s, 3H), 1.32 (t, 3H, J = 7.4 Hz)

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Reference£º
Patent; SMITHKLINE BEECHAM CORPORAITON; OPLINGER, Jeffrey Alan; WO2008/28118; (2008); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles