1,2-Dimethoxyethane → HCID 57917411, compound

Participants

Reaction Steps

In a microwave vial were introduced under argon 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (23 mg, 0.112 mmol) and 6-chloro-3-(4,6-difluoro-1-methyl-1H-indazol-5-ylmethyl)-imidazo[1,2-b]pyridazine (Stage 284.1, 25 mg, 0.075 mmol) with 0.3 mL DME. The solution was degassed with argon, before adding PdCl2(PPh3)2 (1.5 mg) and 2 M K2CO3 (0.101 mL). The RM was then stirred at 80°-90° C. for 30 min. Additional 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (10 mg, 0.048 mmol) and PdCl2(PPh3)2 (1.5 mg) were added. The RM was then diluted with DCM and washed with sat. aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered, evaporated to dryness and the residue was purified (CombiFlash® Companion System®, with RediSep® silica gel column, EtOAc/MeOH=100:0->80:20) to afford the title compound as a beige crystalline powder (tR 3.91 min (conditions 3), MH+=380.2, 1H-NMR in DMSO-d6: 8.36 (s, 1H); 8.18 (s, 1H); 8.05 (s, 1H); 8.02 (d, 1H); 7.50 (m, 2H); 7.45 (s, 1H); 4.40 (s, 2H); 3.97 (s, 3H); 3.90 (s, 3H)).

Provenance & Evidence