Sodium hydride → HCID 54579457, compound

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of compound (3-2) (214 mg; 1.0 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3-3, 194 mg; 1.0 mmol) with NaH 60% dispersion in mineral oil (60 mg; 1.5 mmol) in 3 mL of DMF was stirred at 90° C. for 3 hours. The reaction mixture was partitioned between EtOAc (200 mL) and saturated NaHCO3 solution (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and concentrated by vacuum to give 361 mg of (3-4) as a yellow grease (89% yield). 1H NMR (400 MHz, chloroform-D) δ ppm 1.21-1.34 (m, 12H) 1.39-1.50 (m, 9H) 1.56-1.78 (m, 4H) 3.14 (s, 2H) 3.72-3.91 (m, J=32.34 Hz, 2H) 4.05 (s, 2H) 7.65 (s, 1H) 7.80 (s, 1H) 8.00 (s, 1H). LCMS calcd for C20H34BN3O5 (M+H) 408, found 408. HPLC purity 85%.

Provenance & Evidence