Hydroxyamine hydrochloride → HCID 86609394, compound

Participants

Reaction Steps

[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone (50 mg, 0.085 mmol) and hydroxyamine hydrochloride (29 mg, 0.42 mmol) in 2 mL of ethanol was heated to reflux. After 2 hrs, the reaction was completed. The solvent was removed under reduced pressure. The crude product was redissolved in EtOAc and washed with 5% NaHCO3 (aq) and brine. The organic phase was dried and concentrated to provide [3-(4-Methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)phenyl]-pyridin-3-yl-methanone oxime which was further purified by prep TLC (10:1 EtOAc/MeOH). [3-(4-Methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]pyridin-3-yl-methanone oxime was hydrolyzed as described above to give [3-hydroxy-5-(1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone oxime. NMR for the mixture of isomers: 1H NMR (400 MHz, CD3OD): δ 8.69 (d, J=1.8 Hz, 0.3H), 8.59 (d, J=1.4 Hz, 0.7H), 8.55 (dd, J=5.1, 1.6 Hz, 0.7H), 8.50 (dd, J=4.9, 1.4 Hz, 0.3H), 7.95 (dt, J=5.0, 2.6 Hz, 0.3H), 7.89 (dt, J=4.9, 2.5 Hz, 0.7H), 7.53 (dd, J=7.8, 4.9 Hz, 0.7H), 7.42 (dd, J=8.1, 4.8 Hz, 0.3H), 7.37-7.32 (m, 1H), 7.23 (d, J=3.2 Hz, 0.3H), 7.22 (d, J=3.2 Hz, 0.7H), 7.20-7.00 (m, 5H), 6.91 (dd, J=2.3, 1.6 Hz, 0.7H), 6.79 (dd, J=2.4, 1.4 Hz, 0.3H), 6.59 (d, J=3.1 Hz, 0.3H), 6.49 (d, J=3.2 Hz, 0.7H).

Provenance & Evidence