ethyl(trimethyl)silane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method described in Example S117a, 1-bromo-3-(heptyloxy)benzene (1 g, 4 mmol) was reacted with trimethylsilylethane (0.43 g, 4.4 mmol) to give the title compound as a yellow oil (575 mg, 55%). 1H NMR (400 MHz, CDCl3) δ 7.19 (t, 1H, J=7.6 Hz), 7.05 (d, 1H, J=7.2 Hz), 6.99 (s, 1H), 6.87 (d, 1H, J=7.0 Hz), 3.94 (t, 2H, J=6.8 Hz), 1.79-1.75 (m, 2H), 1.47-1.30 (m, 6H), 0.91 (t, 3H, J=6.8 Hz), 0.26 (s, 9H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method described in S117a, 2-bromo-5-hexylthiophene (1 g, 4 mmol) was reacted with trimethylsilylethane (0.43 g, 4.4 mmol) to give the title compound as a yellow oil (1.07 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.05 (d, 1H, J=3.6 Hz), 6.61 (d, 1H, J=3.6 Hz), 2.77 (t, 2H, J=7.2 Hz) 1.65-1.56 (m, 2H), 1.36-1.30 (m, 6H), 0.89 (t, 3H, J=6.4 Hz), 0.24 (s, 9H).

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2-methoxypyrimidine (500 mg, 2.7 mmol) in ethyl acetate (2 mL) and water (0.2 mL) was added trimethylsilylethane (0.41 mL, 3 mmol), triethylamine (0.75 mL, 5.4 mmol), copper iodide (25 mg, 0.13 mmol) and bis(triphenylphosphine)palladium(II) dichloride (47 mg, 0.067 mmol). The solution was heated to 60° C. for 16 h. Ethyl acetate (100 mL) was added and the solution was washed with water (3×10 mL), dried over MgSO4 and treated with decolorizing charcoal. Ethyl acetate was removed in vacuo to give the title compound as a clear oil (547 mg, 97%). 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 2H), 4.01 (s, 3H), 0.24 (s, 9H). the solution was washed with water (3×10 mL) dried over MgSO4 treated with decolorizing charcoal Ethyl acetate was removed in vacuo