6-METHOXY-3-METHYL-1H-INDAZOLE

To a solution of l-(2-fluoro-4-methoxyphenyl)ethanone (4.85 g, 28.8 mmol) in ethanol (50 mL) was added hydrazine hydrate (5.61 mL, 115 mmoi) and the mixture was heated at reflux temperature for 6 h.This mixture was evaporated to dryness. Then, ethylene glycol (24. 12 rnL, 433 mmol) was added and the mixture was heated at 150°C for 96 h. After cooling to room temperature, the mixture was diluted with water (75 mL). A solid was formed and the suspension was stirred for 30 minutes. After filtration, indazole INT-1A (4.20 g, 26 rnmol, 90percent) was isolated as an off white solid. LCMS: calculated for [M+[-I1: 163, found: 163.1-(2-fluoro-4-methoxyphenyl)ethan-1-one (2 g, 11.9 mmol) was dissolved in 5 mL of a mixture of hydrazine hydrate (85percent) and NMP (15 mL). The mixture was stirred at 120 °C for 24 hours and purified by column chromatography to obtain 6-methoxy-3-methyl-1H-indazole (1.5 g, 78percent).Step A: 6-Methoxy-3-methyl-1H-indazole Acid Preparation 14; 3-Methyl-1 H-indazole-5-carboxvlic acid; A solution of 2-fluoro-4-methoxyactophenone (2.0 g, 12 mmol) in hydrazine hydrate (30 mL) was heated at reflux for two days. The mixture was cooled to room temperature, poured into water and extracted with EtOAc (3x). The organic extracts were concentrated, dissolved in a minimal amount of CHA solution of 2-fluoro-4-methoxyacetophenone (2.0 g, 12 mmol) in hydrazine (30 mL) was heated at reflux for 2 days. The mixture was cooled to room temperature, poured into water and extracted with EtOAc (3x). The combined organic extracts were concentrated, dissolved in a minimum amount of CHTo 2'-fluoro-4'-methoxyacetophenone (5.24 g) was added hydrazine monohydrate (20 mL) at room temperature, and then the reaction mixture was stirred at 140°C for 20 hours. The precipitated solid was filtered to give the titled compound (4.20 g) as a red solid.

Molecular Weight:162.19
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:162.079312947
Monoisotopic Mass:162.079312947
Topological Polar Surface Area:37.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes