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Preparation of tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate Disclosure Number: IPCOM000249801D
Publication Date: 2017-Apr-06
Document File: 1 page(s) / 103K

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Preparation of tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-


Tert-butyl 4-(4-ethyl-3-iodophenyl)-4-methyl-3-oxopentanoate (64.4 g) was dissolved in DMF

(257 ml) and then cesium carbonate (151 g) was added to the solution. The suspension was

stirred and a solution of 4-chloro-3-nitrobenzonitrile (35.3 g) in DMF (129 ml) was added drop

wise. The mixture was heated at 35ºC and hold for 8-10 h. It was cooled down to room

temperature and diluted with AcOEt (322 ml), THF (322 ml) and water (322). Acetic acid (36 ml)

was added drop wise and the aqueous layer was discarded. The organic layer was diluted with

THF (322 ml) and water (322 ml) and sodium hydrosulfite (80.8 g) was added portion wise to the

solution. The mixture was stirred at room temperature for 3 h. The aqueous layer was discarded

and the organic layer was washed with a solution of water (354 ml) and HCl 35% (4.5 ml) first

and then with a solution of water (193 ml) and NaOH 25% (21 ml). The organic layer was

concentrated under reduced pressure. Ethanol (193 ml) was added to the residue and distilled

again. The residue was dissolved in ethanol (238 ml) at 65ºC and water (11 ml) was added drop

wise to precipitate the solid. The mixture was cooled down to 10ºC and the solid was filtered

and washed with ethanol/water.

The previous wet solid was suspended in toluene (385 ml) and the solvent was distilled under

reduced pressure. The process was repeated again until a concentrated solutio...