Dimethylformamide → HCID 86622727, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 314 (1.5 g, 2.59 mmol) in a mixed solvent of 9.0 mL of DMF, 1.0 mL of H2O, and 2.0 mL of EtOH was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.53 g, 5.19 mmol), Na2CO3 (830 mg, 7.78 mmol), and tetrakis(triphenylphosphino)palladium(0) (150 mg, 0.13 mmol). The mixture was stirred at 120° C. under microwave irradiation for 30 min. After cooling, the mixture was diluted with EtOAc (200 mL) and washed with H2O (50 mL) and brine (50 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+M cartridge using 1:1 v/v EtOAc/hexanes as the eluant afforded the product: 1H NMR δ 1.49 (s, 3H), 1.52 (s, 9H), 1.58 (s, 3H), 1.84 (t, J=12.7, 1H), 2.33 (dd, J=6.2, 13.2, 1H), 4.78 (m, 1H), 5.15 (m, 1H), 7.09 (d, J=8.4, 2H), 7.20 (d, J=8.5, 2H), 7.26-7.41 (m, 3H), 7.74 (s, 1H), 7.85 (s, 2H).

Provenance & Evidence