Iodine → HCID 58382149, compound

Participants

Reaction Steps

5-Methoxy-1H-indole (4.50 g, 30.6 mmol) in DMF (50 mL) was treated with KOH (1.80 g, 32.1 mmol) then stirred for about 10 min at rt. Iodine (7.84 g, 30.9 mmol) was added and the mixture was stirred for about 1 h. The NaH (60 wt % in mineral oil, 3.06 g, 76 mmol) was added and the mixture was stirred for about 15 min. The 2-iodopropane (3.67 mL, 36.7 mmol) was added and the mixture stirred for about 1 h. A second portion of 2-iodopropane (1.83 mL, 18.4 mmol) was added then the mixture was stirred for about 15 min. The mixture was treated with water (10 mL) then poured into water (250 mL). The mixture was extracted with Et2O (2×75 mL). The combined organics were washed with water (2×100 mL) then brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 3-iodo-1-isopropyl-5-methoxy-1H-indole (10.5 g, 110%): LC/MS (Table 2, Method a) Rt=2.95 min; MS m/z 316 (M+H)+.

Provenance & Evidence