Sodium Hydroxide → HCID 66584135, compound

Participants

Reaction Steps

To a solution of 39.6 g (127 mmol) of ethyl 5-bromo-4-(3-fluorophenyl)-1H-pyrrole-3-carboxylate in 275 ml of acetonitrile are added 10.1 g (253 mmol) of powdered sodium hydroxide and 1.7 g (5.1 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for a few minutes, followed by adding 34.1 g (152 mmol) of tert-butyl(2-bromoethyl)carbamate (CAS 39684-80-5), and the mixture is then stirred for 17 hours at reflux. After cooling, the solvent is evaporated off under reduced pressure and the residue is taken up in ethyl acetate. The solution is washed with saturated aqueous sodium chloride solution, the organic phase is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure, to give a brown oil, which is crystallized from diisopropyl ether, to give 43 g of ethyl 1-(2-tert-butoxycarbonylaminoethyl)-5-bromo-4-(3-fluorophenyl)-1H-pyrrole-3-carboxylate in the form of a beige-coloured powder after filtering off and drying.

Provenance & Evidence