Water → tert-butyl N-[5-methylsulfanyl-4-[3-[5-methyl-1-(2-trimethylsilylethoxymethyl)benzimidazol-4-yl]phenyl]sulfonylthiophene-2-carboximidoyl]carbamate

Participants

Reaction Steps

A mixture of {[4-(3-dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester. (20 mg, 0.044 mmol, Example 140: step a), 4-Iodo-5-methyl-1-(2-methylsilanyl-ethoxymethyl)-1H-benzoimidazole (21 mg, 0.054 mmol, Example 287: step b) and Pd(PPh3)4 in 1.2 ml of 1:1:2 EtOH/2M Na2CO3/toluene was stirred at 90° C. for 5 h, the cooled to RT. Treated with 3 mL of H2O, the mixture was extracted with EtOAc (3×5 mL)/Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (30% EtOAc/hexane) gave 21 mg (71%) of product as a light yellow solid: 1H-NMR (CDCl3; 400 MHz) δ 8.42 (s, 1H). 8.08 (s, 1H), 8.05 (s, 1H), 8.01 (ddd, 1H, J=7.2, 1.8, 1.7 Hz), 7.71–7.67 (m, 2H), 7.57 (d, 1H, J=8.4 Hz), 7.39 (d, 1H, J=8.7 Hz), 5.64 (s, 2H), 3.57 (t, 2H, J=8.3 Hz), 2.61 (s, 3H), 2.33 (s, 3H), 1.51 (s, 9H), 0.95 (t, 2H, J=8.3), −0.03 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C31H40N4O5S3Si, 673.2, (M+H), found 672.9.

Provenance & Evidence