Triphenylphosphine → HCID 58515063, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-chloro-3-quinolinyl)methanol (500 mg, 2.60 mmol), potassium phosphate tribasic (770 mg, 3.60 mmol), Pd(OAc)2 (30 mg, 0.13 mmol), PPh3 (136 mg, 0.52 mmol) and o-tolylboronic acid (530 mg, 3.90 mmol) in water (4.0 mL) was degassed. DME (13 mL) was added and the mixture was degassed further, then heated at 120° C. for 30 minutes. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 10% aqueous potassium carbonate solution. The aqueous phase was extracted with further EtOAc and the combined organic fractions were dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography (SiO2, 10-40% EtOAc in heptane) then by preparative HPLC (Method 2). The product obtained was partitioned between DCM and 10% aqueous K2CO3 solution. The organic phase was dried (MgSO4) and evaporated in vacuo to give the title compound (240 mg, 37%) as a clear gum. δH (CDCl3) 8.34 (s, 1H), 8.12-8.17 (m, 1H), 7.86-7.91 (m, 1H), 7.69-7.76 (m, 1H), 7.54-7.62 (m, 1H), 7.18-7.37 (m, 4H), 4.52 (br. d, J 4.3 Hz, 2H), 2.40 (br. t, J 5.1 Hz, 1H), 2.07 (s, 3H). LCMS (ES+) 250.1 (M+H)+, RT 3.17 minutes (Method 4).

Provenance & Evidence