1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (Rac)-3-[1-(6-fluoro-1-methyl-1h-indazol-5-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Participants

Reaction Steps

(rac)-6-Chloro-3-[1-(6-fluoro-1-methyl-1H-indazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine (Stage 278.1), 240 mg, 0.728 mmol) was introduced in a microwave reactor together with 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (227 mg, 1.092 mmol) and DME (5 mL). The mixture was purged with argon for 5 min. Tetrakis-(triphenylphosphine)-palladium (42.1 mg) and 2 M Na2CO3 (1.31 mL) were added and the mixture was flushed with argon before being sealed. The RM was submitted to microwave irradiation at 150° C. 30 min. Then it was diluted with EtOAc and washed with water, brine, dried over Na2SO4, filtered and evaporated. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA) to afford the title compound as a white solid (tR 1.03 min (conditions 2), MH+=376) 1H-NMR in DMSO-d6: 8.29 (s, 1H); 8.05 (d, 1H); 7.93 (s, 1H); 7.67 (s, 1H); 7.58 (d, 1H); 7.53 (d, 1H); 7.46 (d, 1H); 7.23 (d, 1H); 4.92 (q, 1H); 3.94 (s, 3H); 3.88 (s, 3H); 1.76 (d, 3H)).

Provenance & Evidence