Potassium bisulfate → HCID 57500360, compound

Participants

Reaction Conditions

Reaction Steps

5.43 ml (2.71 mmol) of potassium bis(trimethylsilyl)amide at −20° C. are added to the solution of 0.80 g (2.47 mmol) of methyl 2-amino-5-[(1-hydroxy-2-methylindolizin-3-yl)carbonyl]benzoate in 12 ml of tetrahydrofuran. After 15 minutes, 1.49 g (4.93 mmol) of tert-butyl[3-(bromomethyl)phenoxy]acetate (CAS 176673-59-9 described in Patent Application WO2004014366) in solution in 2 ml of tetrahydrofuran are added and the mixture is then heated at 40° C. for 12 hours. The reaction medium is poured into a saturated aqueous solution of potassium hydrogen sulphate, and the mixture is extracted with ethyl acetate. The organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. After purification by flash chromatography on silica gel (toluene/ethyl acetate gradient=100/00 to 60/40), 0.92 g (61%) of a yellow oil is obtained.

Provenance & Evidence