7-METHYL(1H)INDAZOLE

3-{2-Methyl-4-[1-(4-trifluoromethylphenyl)-1H-indazol-7- ylmethylsulfanyllphenvHpropionic Acid; Step A; 7-Methyl-lH-indazole; Add tert-butyl nitrite (52 mL) to a solution of commercially available 2, 6- dimethylaniline (25 g, 206 mmol) in chloroform (750 mL) at room temperature under nitrogen, stir the mixture for 20 min and add potassium acetate (40 g, 412 mmol) and 18- crown-6 (5.4 g, 20.6 mmol). Heat the mixture at reflux for 3 h, cool to room temperature and stir for an additional 15 h. Remove the solids from the cooled mixture by vacuum filtration and wash with chloroform (400 mL). Wash the filtrate with water (2 x 250 mL), dry over MgS04 and remove the solvents were removed under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (9: 1), to afford 7-methyl-lH-indazole as an orange solid (23 g, 85percent): IH NMR (CDC13) 8 2.60 (s, 3H), 7.10 (m, 2H), 7.70 (d, 1H), 8. 10 (s, 1H).To a solution of 2-hydroxy-3-methylbenzaldehyde (5 g, 36.7 mmol) inEtOH (30 mL) was added hydrazine hydrochloride (in excess) in a 250 mL flask. The solution was refluxed for 3 h and the solvent was distilled under reduced pressure. Purification of the residue by column chromatography (EtOAc:PE=10:1) on silica gel was performed to give 3.5 g of 7-methyl-1H-indazole, yellow crystals (73percent yield). mp 122-124 °C. 1H NMR (500 MHz, CDCl3) δ 11.50(s, 1H, NH), 8.43 (d, J = 1.4 Hz, 1H), 7.82 (dt, J = 7.5, 1.4 Hz, 1H), 7.43 (t, J = 7.5 Hz, 1H), 7.13 (dd, J =7.5, 1.4 Hz, 1H), 2.50 (s, 3H-CH3).

Molecular Weight:132.16
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:132.068748264
Monoisotopic Mass:132.068748264
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes