Triphenylphosphine → HCID 86599491, compound

Participants

Reaction Steps

A mixture of ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21a, Step 2 (0.500 g, 1.04 mmole), phenylboronic acid (133 mg, 1.09 mmole), Pd(OAc)2 (7.00 mg, 0.031 mmole), triphenyl phosphine (24.4 mg, 0.093 mmole), and NaHCO3 (132 mg, 1.25 mmole) in toluene (25 mL) and H2O (5 mL) was stirred at room temperature for 21 hrs and was then refluxed for 1 h. Pd(PPh3)4 (120 mg, 0.104 mmole) was added and the mixture was refluxed for 1.5 hrs. LCMS indicated that the product was increased slightly. Additional Pd(PPh3)4 (120 mg, 0.104 mmole), NaHCO3 (132 mg, 1.25 mmole) and phenylboronic acid (133 mg, 1.09 mmole) and EtOH (10 mL) to above mixture and the mixture was refluxed overnight. After cooling, the mixture was then poured into brine (100 mL) and extracted with EtOAc (100 mL). The EtOAc layer was separated, dried over MgSO4 and filtered. The crude product was purified by silica chromatography (0-10% EtOAc—hexanes) to give 336 mg (85%, yield) of the product as an off-white solid: EIHRMS m/z 432.0807 (M+, C20H14F6O4, Calc'd 432.0796).

Provenance & Evidence