3-Amino-5-nitroindazole

2-fluoro-5-nitrobenzonitrile (1.0 g, 6.02 mmol) was dissolved in n-butanol (20 mL). Then, hydrazine hydrate (420 μL, 7.22 mmol) was added to the solution. The mixture was stirred at 110° C. for 2 hours and cooled, and then methylene chloride (MC) was added to the reaction mixture, and the formed precipitate was filtered, thereby obtaining the desired compound (84percent yield). 1H NMR (400 MHz, DMSO-d6) δ 8.89 (d, 1H), 8.05 (dd, 1H), 7.34 (d, 2H), 5.98 (s, 2H). Mass=178.15.1st Step To a solution of 5-nitro- l //-indazol-3-amine (200 mg, 1.12 mmol) in pyridine (3 mL) was added butyryl chloride (119.62 mg, 1.12 mmol, 117.28 uL) in ACN (0.2 mL) at 0 C. The mixture was stirred at 25 C for 2 hrs. The mixture was concentrated and taken up in MeOH (6 mL) and filtered. The solid was dried in vacuo to afford the product (193 mg, 606.29 umol, 54.01% yield) as a yellow solid, which was used without further purification.To a solution of 5-nitro-lH-indazol-3-amine (400 mg, 2.25 mmol) in pyridine (6 mL) was added a solution of acetyl chloride (185.07 mg, 2.36 mmol, 168.24 pL) in ACN (2 mL) at 0 C. The reaction mixture was stirred at 0 C for 1 h. LC-MS showed formation of desired product. The mixture was concentrated under vacuum and washed with MeOH (5 mL), filtered and concentrated under vacuum to afford the title compound (328 mg, 1.42 mmol, 63% yield, 96% purity) as an orange solid.Add 1a (53 mg, 0.5 mmol), 2j (89 mg, 0.5 mmol), triethylamine (126 mg, to a 35 mL reaction flask.1.25 mmol), ammonium iodide (108.8 mg, 0.75 mmol) and chlorobenzene (2 mL) were then placed in an oil bath at 120 C for an additional 12 h.The reaction was quenched by the addition of 50 mL of EtOAc (EtOAc)EtOAc. Filter, spin dry, separated by silica gel column (petroleum ether / acetic acid BEster = 15/1) gave a yellow solid product 3j (84.1 mg, 58%).

Molecular Weight:178.15
XLogP3:1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:178.04907545
Monoisotopic Mass:178.04907545
Topological Polar Surface Area:101
Heavy Atom Count:13
Complexity:217
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes