Potassium Carbonate → 4-Amino-2-(2,2-dioxo-2,3,3a,7a-tetrahydro-1H-2lambda6-benzo[c]thiophen-5-yl)-thieno[3,2-c]pyridine-7-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 5-bromo-1,3-dihydro-benzo[c]thiophene 2,2-dioxide (160 mg, 0.65 mmol) 67 (Salor, Milwaukee, Wis.) in DMSO (1 mL) was added bis(pinacolato)diboron (178 mg, 0.70 mmol), KOAc (159 mg, 1.6 mmol) and Pd(dppf)Cl2 DCM complex (22 mg, 0.027 mmol). The mixture was degassed with N2 and heated at 85° C. for 2 h then DMSO (2 mL), H2O (0.5 mL), K2CO3 (223 mg, 1.6 mmol) and 4-amino-2-bromo-thieno[3,2-c]pyridine-7-carboxylic acid amide H2SO4 salt 17 (200 mg, 0.54 mmol) were added. The mixture was stirred at 85° C. for a further 12 h then filtered. The residue was washed with DMSO (2 mL) and the filtrate purified by reverse phase preparative HPLC to yield 68 as a white solid. 1H-NMR (400 MHz, d6-DMSO) δ 8.31 (s, 1H), 8.24 (s, 1H), 8,19 (bs, 1H), 7.97-7.92 (m, 3H), 7.85 (d, 1H), 4.78 (s, 2H), 4.71 (s, 2H).

Provenance & Evidence