Pyrazole → HCID 91086029, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 314(280 mg, 0.48 mmol), pyrazole (65.8 mg, 0.97 mmol), copper(I) oxide (3.5 mg, 0.02 mmol), 2-hydroxybenzaldehyde oxime (33.1 mg, 0.24 mmol), and Cs2CO3 (315 mg, 0.97 mmol) in 10 mL of CH3CN was degassed and stirred at 85° C. for 16 h. The reaction mixture was cooled and diluted with CH2Cl2 (50 mL) and filtered through a cake of Celite. The filtrate was washed with H2O (50 mL) and brine (50 mL). After the phases separated, the organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 3:7 v/v EtOAc/hexanes as the eluant afforded the product: 1H NMR δ 1.46 (s, 3H), 1.50 (s, 9H), 1.55 (s, 3H), 1.18 (m, 1H), 2.29 (m, 1H), 4.76 (br. s, 1H), 5.13 (m, 1H), 6.38 (m, 1H), 6.47 (m, 1H), 7.05 (d, J=8.5, 2H), 7.18 (d, J=8.5, 2H), 7.39-7.72 (m, 5H), 7.90 (m, 1H).

Provenance & Evidence