Tris(1,1-dimethylethyl)phosphine → HCID 29923770, compound

Participants

Reaction Steps

A solution of Pd2dba3 (0.187 g, 0.205 mmol) in dry THF (10 mL) was treated with tri-tert-butylphosphine (2.483 mL, 0.819 mmol) at room temperature. After stirring for 10 min., 5-bromo-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole (1.2 g, 4.09 mmol) in dry THF (10 mL) was added followed by lithium bis(trimethylsilyl)amide 1M THF (10.23 mL, 10.23 mmol) at same temperature. The reaction was placed in a pre-heated oil bath and stirred for 3.5 h at 100° C. in a sealed tube. The reaction was brought to room temperature, quenched with 1 N HCl solution (25 mL) and stirred for 30 min. The reaction was basified with 1 N NaOH solution (50 mL) and product was extracted into ethyl acetate (3×25 mL). The combined ethyl acetate layer was dried (Na2SO4) and solvent was evaporated to obtain crude product. The crude material was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain 3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-amine (0.6 g, 2.62 mmol, 63.9% yield) as a brown foam. ESI-MS (m/z, %): 230 (MH+, 100).

Provenance & Evidence