Methyl iodide → tert-butyl N-[4-[3-(2-chlorophenyl)-5-methoxyphenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

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Reaction Steps

Iodomethane (3 μL, 0.045 mmol) and tetrabutylammonium fluoride (1M in THF, 14 μL, 0.014 mmol) was added to a solution of {[4-(2′-chloro-5-hydroxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 19: step b) 5 mg, 0.009 mmol) in THF. After stirring for 2 hours, the solution was diluted with EtOAc (20 mL). The organic layer was washed with water (2×4 mL) and brine (5 mL), and was dried over MgSO4. Removal of the solvent in vacuo followed by purification of the residue (preparative TLC; 30% EtOAc in hexanes) afforded the title compound (3.1 mg, 62%). 1H-NMR (CDCl3): δ 7.84 (s, 1H), 7.64 (t, 1H, J=1.6 Hz), 7.53 (dd, 1H, J=1.6, 2.6 Hz), 7.47 (m, 1H), 7.33 (m, 3H), 7.21 (dd, 1H, J=1.6, 2.6 Hz), 3.89 (s, 3H), 2.60 (s, 3H), 1.52 (s, 9H). ESI-MS (m/z): Calcd. for C13H13BrN2O3S3: 421.4; found: 421.1.

Provenance & Evidence