Diphenylmethylidenehydrazine → HCID 17952716, compound

Benzophenone hydrazone (232 mg, 1.2 mmol) was added to a solution of potassium t-butoxide (132 mg, 1.2 mmol) in 10 ml of THF. After stirring for 30 min. at ambient temperature under a nitrogen atmosphere, a solution of (5-bromo-2-fluoro-phenyl)-(2-ethoxy-3,5-diisopropyl-phenyl)-methanone (400 mg, 1.0 mmol) in THF (10 mL) was added and the reaction was stirred for 12 h, then quenched with saturated ammonium chloride solution (20 mL) and extracted with ether (2×20 mL). The organic layers were combined, dried over MgSO4 and evaporated to a residue. The residue was dissolved in ethanol (10 mL) and 1N HCl solution (10 mL) and refluxed for 1 h. After cooling, the reaction was partitioned between ether and water. The organic layer was dried over MgSO4 and evaporated to a residue. The residue was purified by silica gel column (10% ethyl acetate in hexanes) to give 5-bromo-3-(2-ethoxy-3,5-diisopropyl-phenyl)-1H-indazole as a clear oil (61.8 mg, 16%). 1H NMR (250 MHz, CDCl3): δ 7.87 (bs, 1H), 7.22-7.02 (m, 3H), 6.55 (bd, 1H, J=9.4), 3.32 (m, 1H), 3.26 (q, 2H, J=7.5), 2.73 (m, 1H), 1.05 (s, 6H), 1.03 (s, 6H), 0.77 (t, 3H, J=7.5). MS [EI+] 401, 403 (M+H)+.

1. stirringthe reaction was stirred for 12 h
2. customquenched with saturated ammonium chloride solution (20 mL)
3. extractionextracted with ether (2×20 mL)
4. dry with materialdried over MgSO4
5. customevaporated to a residue
6. dissolutionThe residue was dissolved in ethanol (10 mL)
7. temperature1N HCl solution (10 mL) and refluxed for 1 h
8. temperatureAfter cooling
9. customthe reaction was partitioned between ether and water
10. dry with materialThe organic layer was dried over MgSO4
11. customevaporated to a residue
12. customThe residue was purified by silica gel column (10% ethyl acetate in hexanes)

ORD record

ord-a6119e1e3ecf40269a6b36b28a8bec90

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348359B2