Dimethylformamide → HCID 59023748, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-benzo[b]thiophen-2-yl-5-bromo-1H-indazole (Preparation #26, 0.25 g, 0.76 mol), tributylphenyltin (0.56 g, 1.52 mmol), triethylamine (0.23 g, 2.28 mmol) and trans-dichloro[bis(triphenylphosphine)]palladium (II) (0.08 g, 0.114 mmol) in N,N-dimethylformamide (4 mL) was purged with carbon monoxide then stirred under an atmosphere of carbon monoxide at about 90° C. in an oil bath for about 2 hours. The solvent was removed in vacuo and the residue was applied to a silica gel column then eluted with dichloromethane/methanol (95:5). The fractions that contained product were combined and triturated with heptane then the solids were collected by filtration and purified by preparative reverse phase HPLC to give (7-Benzo[b]thiophen-2-yl-1H-indazol-5-yl)-phenyl-methanone(23 mg, 8.5%); (DMSO-d6, 400 MHz) δ 13.85 (bs, 1H), 8.49 (bs, 1H), 8.27 (s, 1H), 8.18 (bs, 1H), 8.06 (m, 2H), 7.93 (m, 1H), 7.81 (m, 2H), 7.71 (m, 1H), 7.61 (m, 2H), 7.45 (m, 2H); RP-HPLC (Table 1, Method e) Rt 2.50 min; m/z: (M+H)+ 353.0.

Provenance & Evidence