6-broMo-3-(trifluoroMethyl)-1H-indazole

Hydrazine hydrate (3.5 mL, 45 mmol) was added to a solution of 1-(4-bromo-2-fluorophenyl)-2, 2, 2-trifluoroethanone (1.00 g, 3.69 mmol) in 1-butanol (15 mL). The reaction was heated to reflux for 5 hours, then cooled to room temperature and left stirring overnight. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3.x.). The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-50percent ethyl acetate/heptanes) gave the title compound (310 mg, 32percent) as an off-white solid. 1-lydrazine hydrate (20.0 mL, 412 mmol) was added neat to a stirred solution of ketone INT-2B (9.5 g, 35.0 mmol) in n-butanol (95.0 mL). The reaction mixture was heated under refiux for 3 h. The reaction mixture was cooled to room temperature, diluted with water (500 mL) and extracted with ethyl acetate (3x 200 rnL). The combined organic layers were washed with brine (150 mL), dried on Na2SO4 and evaporated. Purification by flash column chromatography (silica, 5percent -> 50percent ethyl acetate in heptane) gave indazole INT-2C (5.21 g, 19.6 mmol, 56percent) as a pale solid. GCMS: calculated for [M+H]: 264/266, found: 264/266, mono-Br isotope pattern observed.

Molecular Weight:265.03
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:263.95100
Monoisotopic Mass:263.95100
Topological Polar Surface Area:28.7
Heavy Atom Count:14
Complexity:221
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes