Sodium Carbonate → HCID 59305836, compound

Participants

Reaction Steps

The procedure described for 22 (Example 11) was employed using 16 (192 mg, 0.5 mmol), Pd(Ph3P)4 (58 mg, 0.05 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (208 mg, 1.0 mmol), 2N aqueous Na2CO3 (0.5 mL, 1.0 mmol), and THF (3 mL). The reaction mixture was refluxed for 12 h. Aqueous work-up followed by flash column chromatography afforded 170 mg (88%) of the title product 23 as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.73 (s, 1H), 7.56 (s, 1H), 7.37 (d, J=8.0 Hz, 2H), 7.26 (d, J=8.8 Hz, 2H), 7.20-7.16 (m, 4H), 3.92 (s, 3H), 2.02 (s, 2H), 1.97 (s, 2H), 1.29 (s, 2H), 0.95 (s, 6H), 0.93 (s, 6H). LCMS (APCI): m/z 385 (M+H)+.

Provenance & Evidence