Sodium Carbonate → HCID 24871613, compound

Participants

Reaction Conditions

Reaction Steps

2-Phenyl-3-thiophen-2-yl-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. To a solution of 199.8 mg of 2-phenyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 176, Step B) in 3.5 mL of DMF were added 0.6 mL of 2 M aq. Na2CO3 and 75.6 mg of thiophene-2-boronic acid. PdCl2dppf (20.2 mg) was added and the mixture was heated at 80° C. for 16 h. The mixture was poured into water (50 mL) and extracted with CH2Cl2 (3×15 mL) and the combined organic layers were concentrated in vacuo. Chromatography on SiO2 (0 to 50% EtOAc/hexanes) afforded 58.9 mg of the desired compound as a white solid. MS (ESI): exact mass calculated for C22H25N3O2S, 395.17; found, m/z 396.1 [M+H]+.

Provenance & Evidence