Sodium Carbonate → 6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-amine

Participants

Reaction Conditions

Reaction Steps

6-Bromo-1-(phenylsulfonyl)-1H-indazol-4-amine (3 g, 8.52 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (2.28 g, 9.37 mmol), Pd(dppf)Cl2 (0.623 g, 0.852 mmol) and sodium carbonate (2.71 g, 25.6 mmol) were divided equally between 2× microwave vials and each dissolved in 1,4-dioxane (8 mL) and water (8 mL). The vials were heated in the microwave at 110° C. for 15 min, then allowed to cool. The mixtures were combined and filtered through Celite, washing with EtOAc. The resulting mixture was partitioned between water (100 ml) and EtOAc (100 ml) and the layers separated. The aqueous layer was extracted with further EtOAc (2×50 ml) and the organic extracts were combined and the solvent removed in vacuo. The residue (4.6 g) was pre-adsorbed onto silica, which was added to the top of 2×100 g silica SPE cartridges. These were eluted with 0-100% EtOAc/cyclohexane over 60 minutes on the FlashMaster II. The product-containing fractions were combined and the solvent was removed in vacuo to afford the title compound as an orange solid (920 mg).

Provenance & Evidence