Indole → 1-(3-Bromopropyl)indole

To sodium hydride (0.9 g, 30 mmol, 80% oil dispersion) and indole (2.81 g, 24 mmoles) was added anhydrous dimethylformamide (50 mL). The resultant mixture was stirred at room temperature under argon for 1 h. Then neat 1,3-dibromopropane (7.3 mL, 72 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was poured into water (120 mL) and the resultant slurry was extracted with diethyl ether (3×100 mL). After the organic extracts were combined and concentrated in vacuo, the crude material was purified by dry column chromatography (350 mL funnel filled with Silica 10–40μ, Sigma cat. S-6628) using as eluent a mixture of ethyl acetate and hexanes (1:49 v/v, containing 0.2% v/v isopropylamine) to yield 1.43 g of N-(3-bromopropyl)indole.

1. extractionthe resultant slurry was extracted with diethyl ether (3×100 mL)
2. concentrationconcentrated in vacuo
3. customthe crude material was purified
4. customby dry
5. additioncolumn chromatography (350 mL funnel filled with Silica 10–40μ, Sigma cat. S-6628)
6. additiona mixture of ethyl acetate and hexanes (1:49 v/v
7. additioncontaining 0.2% v/v isopropylamine)

ORD record

ord-10055fa779714b37a10e765b996abfbf

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105534B2