Sodium Carbonate → HCID 18186818, compound

Participants

Reaction Steps

1,2-Dimethoxyethane (120 mL) was added to a mixture of tetrakis(triphenylphosphine)palladium (0) (0.87 g, 0.75 mmol) and 2,6-dichloropyrazine (2.43 g, 16.3 mmol). After 15 min of stirring at room temperature, thiophene-3-boronic acid (2.09 g, 16.3 mmol) followed by aqueous Na2CO3 (2 M; 25 mL) were added. The mixture was heated at reflux for 2 h [TLC monitoring by SiO2/n-hexane/ethyl acetate (85:15)]. The layers were separated and the light brownish water layer was extracted with ether (2×100 mL). The combined organic layers were dried (K2CO3), filtered and concentrated in vacuo. The brownish oil obtained was purified by silica gel chromatography (18×5 cm) eluting with n-hexane/ethyl acetate (85:15). This furnished 1.46 g (45%) of the title compound as an off-white solid. HRMS m/z calcd for C8H5ClN2S (M)+ 195.9862, found 195.9868. Anal. (C8H5ClN2S) C, H, N.

Provenance & Evidence