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With sodium cyanoborohydride; acetic acid; at 20.0℃; for 1.0h;Inert atmosphere; Industrial scale;
To a solution of Compound D (3.5 g, 21 mmol) in AcOH (40 mL) was added sodium cyanoborohydride (2.7 g, 43 mmol) and the mixture was purged with N2 for 1 h at room temperature.The reaction was complete by TLC (PE / EA = 10/1), further ethyl acetate EA (200 ml) was added and the mixture was made basic with a 5N NaOH solution (200 ml) at a pH of about 8. The organic layer was separated, Wash once, fullAnd brine once, dried over anhydrous sodium sulfate, dried to give 3.5g of brown solid Compound E, spare. Yield 98%.
1-(6-Chloro-5-methyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
96%
a) 1-(6-Chloro-5methyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone; Using a procedure described in J. Med. Chem. 1991, 34, 140, from 0.250 g (0.002 mol) of <strong>[162100-42-7]6-chloro-5-methyl-1H-indole</strong> were prepared 0.38 g (96%) of the title compound as a white solid.
With copper(l) iodide; In N,N-dimethyl-formamide; at 135.0℃; for 16.0h;Inert atmosphere; Industrial scale;
Compound C (19.4 g, 81.6 mmol), Cul (21.1 g, 111 mmol) and dimethylformamide DMF (250 ml) were sequentially added to the reactor, which was replaced with N 2 and reacted at 135 C for 16 h.The reaction was monitored by TLC (PE / EA = 10/1), cooled to room temperature and poured into ice water (1L), extracted with ethyl acetate (500ml), stirred and filtered to obtain the filtrate. The EA phase was washed once with saturated brine, dried over anhydrous sodium sulfate and spun dry. The residue was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10)Methyl tert-butyl ether (MTBE) (50 ml) was slurried and the filter cake was filtered to give 3.5 g of compound D as a light brown solid in 26% yield for the next reaction.
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