p-Diiodobenzene → 2,2,2-Trifluoro-1-(1-(3-(4-iodophenyl)prop-2-ynyl)-1H-indol-3-yl)ethanone

Participants

Reaction Steps

A mixture of product of Step B (0.25 g, 1 mmol), 1,4 di-iodobenzene (0.4 g, 1.2 mmol) Cl2Pd(PPh3)2 (0.06 g) and catalytic amount of CuI in a mixture of DMF:DIPEA (10 ml: 0.5 ml) at room temperature was degassed under reduced pressure and saturated with N2. This was stirred overnight at room temperature, quenched with NaHCO3 solution and diluted to 50 ml with EtOAc. The organic layer was separated and washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.28 g, 51%), as light yellow solid. 1H-NMR (CDCl3) 8.43-8.40 (b, 1H); 8.12 (b, 1H); 7.66 (t, 2H, J=8.36 Hz); 7.55-7.51 (m, 1H); 7.44-7.38 (m, 2H); 7.14 (d, 2H, J=8.30 Hz); 5.16 (s, 2H).

Provenance & Evidence