indium(III)chloride → HCID 57855969, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of indium trichloride (2.0 g, 9.04 mmol) in 5 ml of dry THF under argon is cooled to −78° C. and then treated drop wise with methyl magnesium chloride (3M in THF, 9.1 ml, 27.12 mmol). The milky suspension is allowed to warm to room temperature and then added drop wise to a refluxing solution of bis(triphenylphosphine)palladium(II)dichloride (0.19 g, 0.27 mmol) and 6-Nitro-5-trifluoromethanesulfonyloxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (4.05 g, 9.042 mmol) in 35 ml of dry THF. The mixture is refluxed under argon, monitoring by TLC. After reaction completion, the reaction mixture is concentrated in vacuo, and the residue taken up in diethyl ether and washed successively with dilute aqueous hydrochloric acid and brine. The diethyl ether phase is dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. The residue (2.9 g) is purified by flash column chromatography, eluting with 4:1 hexane:ethyl acetate. This gives 2.0 g (70%) of the title product as yellow crystals. 1H NMR (CDCl3, 400 MHz): δ ppm: 2.7 (s, 3H); 4.0 (s, 3H); 7.98 (d, 1H); 8.68 (d, 1H); 8.83 ppm (s, 1H). LC/MS: 315 (M+1)+

Provenance & Evidence