Sodium Carbonate → {3-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of [3-(4-amino-5-bromo-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzyl]-carbamic acid tert-butyl ester (2.65 g, 6.1 mmol) in DMF (20 mL), 2-benzyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole (3.26 g, 9.8 mmol), Pd(PPh3)4 (700 mg, 0.6 mmol) and 2 N Na2CO3 (12 mL) were added. The mixture was degassed for 20 min and was then heated to 150° C. in microwave reactor for 10 min. After cooling, the mixture was partitioned between EtoAc/H2O and the organic layer was separated and dried. Biotage® chromatography (50-100% EtOAc) provided the title product as off white solid 2.6 g (76%). NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1 H), 8.05 (d, 2 H), 8.0 (s, 1 H), 7.90 (d, 1 H), 7.70 (s, 1 H), 7.60-7.40 (m, 7 H), 7.25 (d, 1 H), 7.20 (s, 1 H), 5.70 (s, 2 H), 4.10 (d, 2 H), 0.9 (s, 9 H); ES-MS m/z 561.34 [M+H]+, HPLC RT (min) 4.06.

Provenance & Evidence