Dichloromethane → HCID 22388590, compound

Participants

Reaction Conditions

Reaction Steps

[2-(4-Bromophenoxy)propyl][(methylethyl)sulfonyl]amine (200 mg, 0.595 mmol), cyclopentylboronic acid (60 mg, 0.714 mmol), ([1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (4 mg, 0.024 mmol), and 2M sodium hydroxide (1 mL) were combined with THF (4 mL) in a 15 ml round-bottomed flask, fitted with a condenser, and stirbar, in a temperature regulated oil bath, and refluxed at 65° C. overnight in a nitrogen system. After cooling to room temperature, the reaction mixture was quenched with 15 mL of water, and extracted three times with 15 mL ethyl acetate. The organic extractions were combined and dried with magnesium sulfate, then filtered through Celite®, and concentrated in-vacuo, yielding 210 mg viscous black oil. This material was further purified using a 4000 uM rotor on a Chromatotron in a 1:1 hexanes:ethyl acetate solvent system to provide the title compound (50 mg, 16%) as white crystals.

Provenance & Evidence