Sodium Hydroxide → HCID 66585013, compound

Participants

Reaction Steps

To a solution of 3.75 g (20.1 mmol) of 5-fluoro-4-phenyl-1H-pyrrole-3-carbonitrile in 101 ml of acetonitrile are added 1.6 g (40 mmol) of finely ground sodium hydroxide and 0.27 g (0.81 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for a few minutes, followed by adding 5.42 g (24.2 mmol) of tert-butyl(2-bromoethyl)carbamate (CAS 39684-80-5), and the mixture is then stirred for 18 hours at 90° C. After cooling, the solvent is evaporated off under reduced pressure and the residue is taken up in twice 125 ml of water. The product is extracted with ethyl acetate. The organic phase is then washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a mixture of 15 to 50% ethyl acetate in cyclohexane, to give 2.5 g of tert-butyl{2-[4-cyano-2-fluoro-3-phenyl-1H-pyrrol-1-yl]ethyl}carbamate in the form of a brown oil.

Provenance & Evidence