反应详情

Sodium hydride (0.23 g of a 60% dispersion in oil) was added to a solution of ethyl 5-acetoxyindole-2 carboxylate (1.29 g) and tetra-n-butylammonium iodide (10 mg) in anhydrous DMF (25 ml) under a stream of argon. The reaction mixture was stirred for 15 minutes and a solution of 4-chloro-3-iodobenzyl bromide (1.9 g) in DMF (5 ml) was added. The mixture was stirred for 15 hours, then saturated aq. ammonium chloride (5 ml) was added. The residue obtained on removal of the solvent was diluted with saturated aq. ammonium chloride (50 ml) and extracted with ethyl actate (3×30 ml). The combined ethyl acetate extracts were washed with brine (100 ml) and dried. The residue obtained on removal of the solvent was purified by chromatography on silica eluting with a mixture of ethyl acetate and iso-hexane (1:9) to give the title compound (0.21 g). NMR (CD3SOCD3): d 1.1 (t, 3H), 2.2 (s, 3H), 4.3 (m, 2H), 5.8 (s, 2H), 6.9 (m, 1H), 7.1 (m, 1H), 7.35 (m, 1H), 7.4 (m, 2H), 7.6 (m 2H), 7.7 (m, 2H); m/z 497.5 (M+H).

1. stirringThe mixture was stirred for 15 hours
2. customThe residue obtained on removal of the solvent
3. extractionextracted with ethyl actate (3×30 ml)
4. washThe combined ethyl acetate extracts were washed with brine (100 ml)
5. customdried
6. customThe residue obtained on removal of the solvent
7. customwas purified by chromatography on silica eluting with a mixture of ethyl acetate and iso-hexane (1:9)