Tetramethyltin → HCID 70159519, compound

Participants

Reaction Steps

Triphenylphosphine (66 mg, 0.2 mmol) was added in one portion to a stirred solution of palladium(II) acetate (18 mg, 0.06 mmol) in tetrahydrofuran (2.5 mL) under Ar. The mixture was stirred for 5 min then a solution of (S)-1-[2-(tert-butoxycarbonylamino)propyl)-5-fluoro-6-iodoindoline (0.45 g, 1.1 mmol) in tetrahydrofuran (7.5 mL) was added in one portion. The mixture was stirred for 10 min then tetramethyltin (2.0 g, 11 mmol) was added in one portion. The mixture was heated to reflux and stirred for 168 h. After cooling to room temperature, the mixture was poured into an aqueous solution of potassium fluoride (50 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo to leave a crude oil. The oil was purified by column chromatography [SiO2; ethyl acetate-heptane (1:19)] to give the product (0.17 g, 50%) as a yellow solid; NMR δH (400 MHz, CDCl3) 6.74 (1H, d, J 9 Hz), 6.22 (1H, d, J 5.9 Hz), 4.57 (1H, br. s), 3.82-3.91 (1H, m), 3.31-3.40 (2H, m), 2.89-2.99 (4H, m), 2.05 (3H, s), 1.44 (9H, s), 1.22 (3H, d, J 6.5 Hz).

Provenance & Evidence