Cesium carbonate → Methyl 4-[(4-cyclohexylphenyl)amino]-5-methylthiothiophene-2-carboxylate

Participants

Reaction Steps

The same procedure as in Example 197, step (a) was followed using 122 mg (0.457 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate (as prepared in Example 241, step (a)), 9.9 mg (9.7 mol %) of palladium (II) acetate, 42.3 mg (14.9 mol %) of racemic-BINAP, 206 mg (0.632 mmol) of cesium carbonate, 102 mg (0.582 mmol) of 4-cyclohexylaniline and 913 μL of toluene, and chromatographed as before using 20-40% CH2Cl2-hexane to afford 73.8 mg (45%) of the title compound as a light green resin: 1H-NMR (CDCl3, 400 MHz) δ7.74 (s, 1H), 7.15 (d, 2H, J=8.4 Hz), 6.98 (d, 2H, J=8.4 Hz), 6.12 (s, 1H), 3.88 (s, 3H), 2.48 (m, 1H), 2.39 (s, 3H), 1.87 (m, 4H), 1.76 (br d, 1H, J=12.5 Hz), 1.41 (m, 4H) and 1.28 (m, 1H). Mass spectrum (ESI, m/z): Calcd. for C19H23NO2S2, 362.1 (M+H), found 362.4.

Provenance & Evidence