Sodium Carbonate → 3-[1-Benzenesulfonyl-3-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

3-(1-Benzenesulfonyl-3-iodo-1H-indol-5-yl)-but-2-enoic acid methyl ester (653 mg, 1.35 mmol) and (2-butoxy-3,5-diisopropylphenyl)-boronic acid (415 mg, 1.49 mmol) were dissolved in toluene (8 mL) under a nitrogen atmosphere. Tetrakis(triphenylphosphine) palladium (172 mg, 0.15 mmol) and 2N Na2CO3 (2.7 mL) was added and the biphasic mixture stirred at 80° C. for 6 h. The reaction was judged complete by TLC (9:1) in hexane:ethyl acetate but was allowed to stir overnight at room temperature. The reaction was diluted with water (5 mL)/ethyl acetate (15 mL). The layers were separated and the aqueous washed with ethyl acetate (10 mL). The organic portions were passed through a pad of Celite, dried (MgSO4), filtered and concentrated in vacuo to provide 1.20 g of a dark brown oil. Chromatography (SiO2, hexanes/ethyl acetate) provided 294 mg (37%) of a yellow foam. 1H NMR (250 MHz, CDCl3): δ 8.06 (d, 1H, J=8.7), 7.94 (m, 2H), 7.80 (s, 1H), 7.75 (d, 1H, J=1.7), 7.56-7.45 (m, 4H), 7.13 (m, 2H), 6.14 (d, 1H, J=1.2), 3.75 (s, 3H), 3.39 (sep, 1H, J=6.9), 3.29 (t, 2H, J=6.3), 2.93 (sep, 1H, J=6.9), 2.60 (d, 3H, J=1.2), 1.29 (d, 7H, J=6.9), 1.27 (d, 7H, J=6.9), 1.22 (m, 2H), 0.62 (t, 3H, J=7.2). MS [EI+] 588 (M+H)+.

Provenance & Evidence