Pyrrolidine → HCID 69775100, compound

Participants

Reaction Steps

A solution of 40 mg (0.08 mmol) (RS, SR)-2-(3-bromo-benzenesulfonyl)-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester (example 103) in toluene was treated with 13 mg (0.13 mmol) of NaOtBu, 2 mg (0.007 mmol) of 2-(di-tbutylphosphino)biphenyl, 0.03 mL (0.4 mmol) of pyrrolidine and 4 mg (0.004 mmol) of tris(dibenzylideneacetone)dipalladium. The resulting suspension was stirred at 80° for 4 hrs, treated with a diluted aqueous NaHCO3-solution and extracted twice with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated to give 14 mg (35%) of (RS, SR)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-2-(3-pyrrolidin-1-yl-benzenesulfonyl)-propionic acid methyl ester as a light brown solid, MS: 488 (MH+).

Provenance & Evidence