Tris(1,1-dimethylethyl)phosphine → HCID 59332876, compound

Participants

Reaction Conditions

Reaction Steps

Potassium tert-butoxide (18 mL, 18 mmol) was added to a THF (120 mL) solution of 3-(2-bromo-pyridin-3-yloxy)-propylamine (2.75 g, 11.9 mmol). The solution was purged with an Ar stream for 10 min, bis(dibenzylideneacetone)palladium (342 mg, 0.6 mmol) and tri-tert-butylphosphine (2.1 mL, 0.7 mmol, 10% in hexane) were added and the mixture was stirred at 60° C. for 5 h. The solvent was evaporated, the residue was dissolved in CH2Cl2. This solution was washed with water, dried and evaporated. Chromatographic purification (silica, 0-2% MeOH in CH2Cl2) afforded 0.75 g (42%) of the title compound. 1H NMR (300 MHz, DMSO-d6, 8): 7.70 (dd, J=4.8, 1.4 Hz, 1H), 7.09 (dd, J=7.7, 1.4 Hz, 1H), 6.60 (dd, J=4.8, 7.7 Hz, 1H), 6.02 (s, br, 1H), 4.06 (t, J=5.5 Hz, 2H), 3.21 (m, 2H), 1.90 (m, 2H).

Provenance & Evidence