Sodium Carbonate → HCID 58529505, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 5-bromo-7-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (3.00 g, 7.51 mmol), 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (3.77 g, 11.3 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium(II) dichloromethane adduct (550 mg, 0.75 mmol) in degassed DME (50 mL) was added aqueous Na2CO3 solution (2 M, 11.3 mL). The reaction was heated (80° C.) for 17 h and then cooled to rt. The mixture was partitioned between ethyl acetate (75 mL) and water (75 mL) and the layers were separated. The aqueous phase was further extracted with ethyl acetate (2×75 mL). The combined organics were filtered to remove a fine precipitate, dried (Na2SO4), and concentrated. The crude material was purified by ISCO® chromatography using a gradient of 25 to 75% ethyl acetate in hexanes to afford 1.9 g (48%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.51 (s, 1 H), 7.85 (s, 1 H), 7.77 (dd, 1 H), 7.57-7.54 (m, 1 H), 7.35-7.25 (m, 5 H), 7.11 (dd, 1 H), 6.55 (s, 1 H), 5.63 (s, 2 H), 3.59 (t, 2 H), 2.88 (t, 2 H), 1.79-1.68 (m, 2 H), 1.58-1.48 (m, 2 H), 0.83 (s, 9 H), 0.00 (s, 6 H); ES-MS m/z 527.3 [M+H]+, HPLC RT (min) 3.62.

Provenance & Evidence