Analyzing the synthesis route of 5-Bromo-1H-pyrrolo[2,3-b]pyridine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-35-7, its application will become more common.

Synthetic Route of 183208-35-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 183208-35-7 as follows.

To a stirring solution of aluminum chloride (6.77 g, 50.75 mmol) suspended in anhydrous CH2Cl2 (100 mL) under N2 was added 5-bromo-1H -pyrrolo[2,3-delta]pyridine (2.00 g, 10.15 mmol). The reaction solution was stirred for 1 hour at ambient temperature whereupon acetyl chloride (3.61 mL, 50.75 mmol) was added dropwise and the resulting solution was stirred for 5 more hours. The reaction was cooled to 0 C in an ice bath and quenched carefully by addition of MeOH until the solution became clear. The reaction was concentrated under vacuum. H2O was added and 1 N NaOH was added dropwise until the pH = 4. The product was extracted into ethyl acetate and the organic layer was washed with a saturated solution of sodium potassium tartrate to remove any remaining aluminum salts. The organic layer was dried over Na2SO* and concentrated under vacuum. The material was redissolved in ethyl acetate and filtered through a bed of silica gel. The filtrate was concentrated to afford the title compound as an orange solid (2.25 g, 93% yield). 1H NMR (500 MHz, ^-DMSO) delta 12.70 (br s, 1H), 8.56 (d, J = 2.5 Hz, 1H),8.55 (s, 1H), 8.40 (d, J = 2.5 Hz, 1H), 2.46 (s, 3H). MS: m/z 238.9/240.9 (M + H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-35-7, its application will become more common.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2008/124849; (2008); A2;,
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