6-BROMO-3-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE

A mixture of [5-BROMO-PYRIDIN-2-YL-HYDRAZINE] (4.34 g, 23.1 [MMOL)] and isobutyryl chloride (21.8 mL, 0.208 mol) is refluxed gently for 3 hours. The mixture is then cooled to room temperature. Hexane (22.0 mL) is added and the resulting slurry stirred at room temperature for 15 minutes and filtered. The filtrate cake is washed with hexane (3x) and dried in a vacuum-oven (30-35 [°C)] for 48 hours. The product (5.90 g, yield 92.3percent) may be obtained as an off-white powder. A biphasic mixture of the product (5.87 g, 21.2 [MMOL), ] water (12.0 mL) and dichloromethane (18.0 mL) is cooled to 5 to [10 °C.] A 1N aqueous solution of [NAOH] (21.5 mL) is added over a period of 10 minutes. The mixture is stirred in the bath for 15 minutes. The organic layer is isolated and the aqueous layer extracted with [DICHLOROMETHANE] (2x). The combined organic extracts are washed with 1: 1 brine-water and dried [(MGS04).] Most of the [DICHLOROMETHANE] is removed in vacuo. Ethyl acetate (8.0 mL) is added. After removing about half of the solvent, hexane (32.0 mL) is added. The slurry is stirred in an ice-water bath for 2 hours and filtered. The cake is washed with 9: 1 hexane-ethyl acetate (3x) and dried in a vacuum-oven (30-35 [°C)] for 18 hours. The title compound may be obtained as a sandy tan powder (4. 72g, 92.5percent).A mixture of [5-BROMO-PYRIDINE-2-YL-HYDRAZINE] (4.34 g, 23.1 [MMOL)] and isobutyryl chloride (21.8 mL, 0.208 mol) is [REFLUXED] gently for 3 hours. The mixture is cooled to room temperature. Hexane (22.0 mL) is added and the slurry is stirred at room temperature for 15 minutes and filtered. The cake is washed with hexane (3x) and dried in a vacuum-oven (30- [35°C)] for 48 hours. The product (5.90 [G, ] yield 92.3percent) is obtained as an off-white powder. A biphasic mixture of the product (5.87 [G, ] 21.2 [MMOL), ] water (12.0 mL) and dichloromethane (18.0 mL) is cooled to 5-10 [°C.] A [1N] aqueous solution of [NAOH] (21.5 mL) is added over a period of 10 minutes. The mixture is stirred in the bath for 15 minutes. The organic layer is isolated and the aqueous layer extracted with dichloromethane (2x). The combined organic extracts are washed with 1: 1 brine-water and dried [(MGS04). MOST] of the dichloromethane is removed in vacuo. Ethyl acetate (8.0 mL) is added. After removing about half of the solvents, hexane is added. The slurry is stirred in an ice-water bath for 2 hours and filtered. The cake is washed with 9: 1 hexane-Ethyl acetate (3x) and dried in a vacuum-oven [(30-35°C)] for 18 hours. The title compound may be obtained as a sandy tan powder (4.72g, 92.5percent).A suspension of the product of preparation 29 (16 g, 62 mmol) in phosphorus oxychloride (320 mL) was heated at 75° C. for 18 hours.

Molecular Weight:240.10
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:239.00581
Monoisotopic Mass:239.00581
Topological Polar Surface Area:30.2
Heavy Atom Count:13
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes