Tetrabutylammonium Fluoride → HCID 15604426, compound

Participants

Reaction Steps

To pyridin-3-yl-[3-(1-triisopropylsilanyl-1H-indol-4-yl)-5-triisopropylsilanyloxy-phenyl]-methanone (64 mg, 0.102 mmol) in 2 mL of THF was added 2 mL of MeMgCl (1 M in THF) at 0° C. After 30 min TLC indicated the completion of the reaction. Brine was then added to quench the reaction. The aqueous phase was then extracted with EtOAc. The combined organic phases were dried and concentrated to afford the crude product. The residue was again dissolved in 2 mL of THF and followed by addition of 1 mL of TBAF (3M in THF) at 0° C. After 30 min the solvent of the reaction was removed under reduced pressure. The residue was dissolved in EtOAc and the organic phase washed with water and brine, dried and concentrated to afford the crude product. The crude product was then purified by prep. TLC to afford 3-(1-hydroxy-1-pyridin-3-yl-ethyl)-5-(1H-indol-4-yl)-phenol (13 mg, 39% over two steps). 1H NMR (400 MHz, CD3OD): δ 8.66 (d, 1H, J=1.6 Hz), 8.36 (d, 1H, J=4.0 Hz), 7.93 (d, 1H, J=6.4 Hz), 7.36 (dd, 1H, J=8.0, 4.8 Hz), 7.33 (d, 1H, J=8.0 Hz), 7.21 (d, 1H, J=2.8 Hz), 7.20-7.19 (m, 1H), 7.11 (t, 1H, J=8.0 Hz), 7.01 (d, 1H, J=7.2 Hz), 6.99-6.98 (m, 1H), 6.99 (t, 1H, J=1.6 Hz), 6.46 (d, 1H, J=3.6 Hz), 1.98 (s, 3H).

Provenance & Evidence