Water → 2-(6'-(4-(9H-carbazol-9-yl)phenyl)-3,3'-bipyridin-6-yl)benzo[d]thiazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 7 (0.841 g, 1.89 mmol), 9 (0.549 g, 1.89 mmol), tetrakis(triphenylphosphine)palladium(0) (109 mg, 94.2 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) was degassed with argon for about 20 min while stirring. The stirring reaction mixture was then maintained under argon at about 80° C. for about 18 h. Upon confirming consumption of the starting materials by TLC (SiO2, CH2Cl2), the mixture was cooled to RT and poured over CHCl3 (300 mL). The organics were then washed with sat. NaHCO3, H2O and brine, dried over MgSO4, filter and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO2, 100% CH2Cl2 to 49:1 CH2Cl2-acetone) provided 19 (0.72 g, 72%) as a light yellow solid.

Provenance & Evidence