Nitrogen → 5-ethynyl-1-methyl-1H-indole

참여 물질

반응 단계

5-iodo-1-methyl-1H-indole (1.5 g, 5.84 mmol) were dissolved in mixture of CH2Cl2 (10 ml) and NEt3 (5 ml) and the system was evacuated-back filled by N2 thrice. Pd(PPh3)2Cl2 (122 mg, 3% mol) and TMS-acetylene (0.858 g, 8.7 mmol) were added to it and again flushed N2 into the system. CuI (89 mg, 8% mol) was added and flushed N2 very quickly and reaction was stirred under positive pressure of N2 until reaction completed by TLC (ca. 3 hours). The reaction mixture was diluted with 10 ml of hexane and filtered through celite plug, purified by passing through small column and then suspended in MeOH (20 ml) containing 10 ml of THF. NaOH was added to reaction mixture and stirred at room temp until starting material consumed completely. The reaction mixture was concentrated to 10 ml and extracted with EtOAc from aqueous NH4Cl solution, which was purified by column chromatography; Yield (60%); 1H NMR (300 MHz, CDCl3) δ: 3.03 (s, 1H), 3.73 (s, 3H, NMe), 6.45 (d, J=3.0 Hz, 1H), 7.05 (d, J=3.0 Hz, 1H), 7.23 (d, J=9.0 Hz, 1H), 7.33 (dd, J=9.0, 1.2 Hz, 1H), 7.80 (bs, 1H).

출처 및 근거