Benzo(B)Thiophene-2-Boronic Acid → HCID 86686452, compound

Participants

Reaction Conditions

Reaction Steps

To a deaerated solution of 4-(methylsulfinyl)-1-(pentan-2-yl)-1H-indol-5-yltrifluoromethanesulfonate 17) (0.40 g, 1.0 mmol) and benzo[b]thiophen-2-ylboronic acid (18) (0.35 g, 2.0 mmol), and Pd(PPh3)4 (60 mg, 0.05 mmol) in toluene (10 mL) was added aqueous K2CO3 (2M, 6.0 mL). The mixture was heated at 90° C. for 4 h. Toluene (20 mL) was added and the organic phase was washed with water (20 mL) and then concentrated to dryness in vacuo. The residual was purified by silica gel column chromatography (2:1 hexanes/ethyl acetate) to give 5-(benzo[b]thiophen-2-yl)-4-(methylsulfinyl)-1-(pentan-2-yl)-1H-indole (19) (0.26 g, 68%) as a yellow oil. 1H NMR (500 MHz, CD2Cl2): δ 7.88 (d, J=8.0, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.40 (m, 4H), 7.35 (d, J=3.5, 1H), 7.2 9s, 1H), 4.62 (m, 1H), 3.00 (d, 3H), 1.88 (m, 2H), 1.57 (m, 3H), 1.24 (m, 2H), 0.93 (m, 3H). Mass (ESI, M+H): 382.7. See also Im, G-Y. J., et al., J. Am. Chem. Soc., 132:17933 (2010).

Provenance & Evidence