1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 86721864, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-N-isobutyl-methanesulfonamide (150 mg, 36 μmol), 1-methanesulfonylpiperazine (59.2 mg, 361 μmol), Pd2(dba)3 (33 mg, 36 μmol), XantPhos (20.9 mg, 36 μmol), and sodium tert-butoxide (104 mg, 1.08 mmol) in toluene (3 mL) was degassed with nitrogen then heated at 120° C. for 30 minutes in a microwave reactor. Water was added and the reaction extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated and purified by silica gel column chromatography (0-50% EtOAc in cyclohexane) then freeze dried to give the title compound (22.4 mg). 1H NMR (400 MHz, DMSO): δ 7.33-7.34 (m, 4H), 7.22 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.5 Hz, 2H), 4.37 (s, 2H), 3.45 (d, J=7.3 Hz, 2H), 3.22-3.27 (m, 8H), 2.92 (s, 3H), 1.44-1.46 (m, 1H), 0.82 (d, J=6.6 Hz, 6H). LCMS (m/z, Method B) ES+ 499.9 [M+1]+.

Provenance & Evidence