Indole → HCID 71683083, compound

Participants

Reaction Steps

A round bottom flask containing indole (0.22 mL, 1.70 mmol, 1 equiv) in DMF at R.T. was stirred with KOH (0.10 g, 1.78 mmol, 1.05 equiv) for about 15 min and then treated with I2 (0.44 g, 1.73 mmol, 1.02 equiv). After 30 min, NaH (0.082 g, 2.04 mmol, 1.2 equiv) was added portion-wise. After additional 15 min had passes 1-bromobutane (0.2 mL, 1.87 mmol, 1.1 equiv) was added and the reaction mixture was stirred until completion. Upon completion (TLC monitoring), H2O was added and allowed to stir for 15 min, upon which the mixture was extracted with DCM and the layers were separated. Aqueous layer was washed with DCM (3×) and the combined organic layers were washed with H2O (2×), dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using EtOAc/n-hexanes to afford 0.449 g (80% yield) as an clear oil with a yellow tint. TLC system: 10% EtOAc/90% n-hexanes. 1H NMR (400 MHz, CDCl3) δ 7.18 (d, J=8.8, 1H), 7.11 (s, 1H), 6.88 (dd, J=2.5, 8.8, 1H), 6.84 (d, J=2.4, 1H), 4.05 (t, J=7.1, 2H), 3.87 (d, J=3.7, 3H), 1.81-1.71 (m, 2H), 1.29 (tt, J=5.2, 10.1, 3H), 0.91 (t, J=7.4, 3H).

Provenance & Evidence