New downstream synthetic route of 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine

Synthetic Route of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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.

To a 500 mL round bottom flask containing 75 mL dry THF was dissolved 5- bromo-3-methyl-1 /-/-pyrazolo[3,4-c]pyridine (5.5 g, 25.9 mmol), and the contents were cooled to -15 0C. Sodium hydride (1.24 g (60% by wt., 31.1 mmol) was slowly added in portions to the cold stirring mixture, wherein vigorous gas evolution was observed (NOTE: Use caution during handling and addition of sodium hydride). After stirring for 15 min, benzenesulfonyl chloride (3.66 ml_, 28.5 mmol) was added dropwise via syringe. After stirring 15 min, the contents were removed from the cold bath and stirred with warming to room temperature over a 3 h period. The reaction mixture was poured onto a vigorously stirred solution of ice:water (1 :1 , 500 g), upon which the solid product crashes out. After stirring an additional 10 min, the heterogenous mixture was vacuum filtered and the filter cake was washed with additional water. The resultant solid was triturated with methanol (30 ml_), and the title compound is obtained as an off-white solid (10.75 g, 82%). 1H NMR: (CD3OD- d4) 9.27 (s, 1 H), 8.05 (s, 1 H), 8.01 (d, 2H), 7.69-7.73 (m, 1 H), 7.57-7.61 (m, 2H), 2.53 (s, 3H) ; LC/MS (MH+) = 351.8, 353.8; RT = 2.05 min.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32651; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem