4-Methoxy-alpha-toluenethiol → HCID 67159624, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of title compound from Example 243 Step A (2.74 g, 5.23 mmol), 4-methoxy α-toluenethiol (0.88 mL, 6.28 mmol) in 1,4-dioxane (75 mL) were added DIEA (1.83 mL, 10.5 mmol), Xantphos (0.61 g, 1.05 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.48 g, 0.52 mmol), and the reaction mixture was heated at 90° C. After 15 h, the reaction mixture was allowed to cool to ambient temperature, then was diluted with hexane. The resulting yellow solid was removed by filtration, and the collected organic filtrate was concentrated in vacuo. Purification by flash chromatography on silica gel (5 to 20% ethyl acetate in hexanes) provided the title compound: LCMS m/z 528.6 [M+H]+; 1H NMR (500 MHz, CD2Cl2) δ 8.11 (s, 1H), 7.94 (t, J=7.9 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.36 (m, 2 H), 7.17 (d, J=8.0 Hz, 1H), 7.04 (d, J=8.5 Hz, 2H) 6.74 (d, J=8.7 Hz, 2H) 4.35 (q, J=7.1 Hz, 2H), 3.87 (s, 2H), 3.73 (s, 3H), 2.37 (s, 3H), 1.37 (t, J=7.1 Hz, 3H).

Provenance & Evidence