Triphenylphosphine → HCID 53329539, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (710 mg, 2.000 mmol, prepared as in Example 2, Step 1-2), (3-chloro-2-iodophenyl)(pyrrolidin-1-yl)methanone (671 mg, 2 mmol), Pd(OAc)2 (22.45 mg, 0.100 mmol), triphenylphosphine (52.5 mg, 0.200 mmol) and potassium phosphate (0.331 mL, 4.00 mmol). The vial was evacuated and backfilled with nitrogen gas 3×. ACN (8 mL) and water (2 mL) were added and the reaction mixture was heated to 60° C. overnight in an oil bath. The product precipitated out of solution and was filtered off, dissolved in DCM/MeOH, washed with water and dried over MgSO4. The solvent was removed and the solid was dried under vacuum at 50° C. This material was further purified by preparative HPLC (10-100%; water with 0.1% TFA/CH3CN, 11 min). The obtained product was eluted on an SCX cartridge with MeOH followed by 2M NH3 in MeOH. The basic fraction was concentrated to afford the titled compound as a light-yellow solid. MS (ESI, pos. ion) m/z: 437 (M+1).

Provenance & Evidence