Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate

to compound 139a (3 g, 17.5 mmol) was added pocl3 (21.5 g, 140.2 mmol, 13 ml) in one portion. Then tea (1.8 g, 17.5 mmol) were added. The mixture was stirred at 110 °C for 24 hours under N2. Then ice water (15 ml) was added in to the mixture, and the aqueous phase was extracted with EtOAc (25 ml x 3), the combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give intermediate compound 139b (2.6 g, 13.7 mmol, yield: 78.2percent) as brown oil. 1H NMR (400mhz, CDCl3) δ 4.36 (q, = 7.1 hz, 2h), 2.48 (s, 3h), 1.38 (t, 7 = 7.2 hz, 5h).[0862] to compound 139a (3 g, 17.5 mmol) was added pocl3 (21.5 g, 140.2 mmol, 13 ml) in one portion. Then tea (1.8 g, 17.5 mmol) were added. The mixture was stirred at 110 C for 24 hours under N2. Then ice water (15 ml) was added in to the mixture, and the aqueous phase was extracted with EtOAc (25 ml x 3), the combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give intermediate compound 139b (2.6 g, 13.7 mmol, yield: 78.2%) as brown oil. 1H NMR (400mhz, CDCl3) delta 4.36 (q, = 7.1 hz, 2h), 2.48 (s, 3h), 1.38 (t, 7 = 7.2 hz, 5h).[1097] to a mixture of [0863] to a mixture of compound 139b (400 mg, 2.1 mmol) and 2h-indazole (299 mg, 2.5 mmol) in DMF(3 ml) was added K2CO3 (1.2 g, 8.4 mmol) in one portion. The mixture was stirred at 80 C for 12 hours. Then H2O (9ml) was added into the mixture, and the aqueous phase was extracted with EtOAc (15 ml x 3), and the combined organic layer was concentrated to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate = 300: 1 to 40: 1) to give compound 139c (340 mg, yield: 59.4%) as a pale yellow solid. 1H NMR (400mhz, CDCl3) s 8.33 (s, 1h), 7.82 (d, = 7.9 hz, 1h), 7.68 (d, = 8.8 hz, 1h), 7.57 - 7.51 (m, 1h), 7.35 (t, j = 7.7 hz, 1h), 4.24 (q, j = 7.0 hz, 2h), 2.56 (s, 3h), 1.13 (t, = 7.2 hz, 3h).

Molecular Weight:189.59
XLogP3:1.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:189.0192708
Monoisotopic Mass:189.0192708
Topological Polar Surface Area:52.3
Heavy Atom Count:12
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes