Iodine → HCID 58382149, compound

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)+.

1. stirringthe mixture was stirred for about 1 h
2. stirringthe mixture was stirred for about 15 min
3. stirringthe mixture stirred for about 1 h
4. stirringthe mixture was stirred for about 15 min
5. extractionThe mixture was extracted with Et2O (2×75 mL)
6. washThe combined organics were washed with water (2×100 mL)
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-b9899bc8e7a54975bc107ccd26606382

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785639B2