Ethyl 1H-indole-3-acetate → tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate

To a solution of ethyl 2-(1H-indol-3-yl)acetate (5 g, 24.6 mmol) in 25 ml of DCM was added N-bromosuccinimide (4.38 g, 24.6 mmol) in small portions at 0° C. The mixture was warmed to room temperature and stirred for 6 hours. Di-tert-butyl pyrocarbonate (10.74 g, 49.2 mmol), DIPEA (8.6 ml, 49.5 mmol) and DMAP (cat) was added to the mixture. The reaction was stirred overnight. The mixture was diluted with DCM (100 ml) and washed with HCl (0.5 N, 2×50 ml). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography on silica (5-20 EtOAc/hexanes) to get 6.3 g (16.5 mmol) of product. MS (m/z) 382 [M+H]+.

1. stirringThe reaction was stirred overnight
2. washwashed with HCl (0.5 N, 2×50 ml)
3. dry with materialThe organic layer was dried with Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. additionThe crude product was introduced to a silica gel loading column
7. custompurified by column chromatography on silica (5-20 EtOAc/hexanes)

ORDレコード

ord-1e14f1328bbf4979b2146d42f154a45f

出典データセット

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09012441B2