Downstream synthetic route of 434958-85-7

434958-85-7 N-Boc-5-Hydroxyindole 22596220, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.,434958-85-7

General procedure: A suspension of bismacycle tosylate 1-OTs (1.0 equiv.; initial concentration = 0.05 M),K2CO3 (1.2 equiv.) and arylboronic acid (1.1 equiv.) in toluene/water (99:1,v/v) was stirred at 60 C for 2 h. After cooling to room temperature, substrates(naphthols, 0.90 equiv.; phenols, 3.0 equiv.) and mCPBA (titrated; 1.5 equiv.) were added. The reaction was stirred for 10 min at room temperature and then methanol (2 ml) was added. The mixture was diluted with diethyl ether and washed witha saturated aqueous solution of KHCO3. The organic phase was separated, dried (MgSO4), filtered and concentrated in vacuo before purification by flash column chromatography on silica gel. Following isolation of the desired arylation product, bismacycle acetate 1-OAc can be recovered by flushing the column with diethyl ether to remove organic impurities before elution with 2% acetic acid in methanol.

434958-85-7 N-Boc-5-Hydroxyindole 22596220, aindole-building-block compound, is more and more widely used in various fields.

Reference:
Article; Ball, Liam T.; Jurrat, Mark; Lewis, William; Maggi, Lorenzo; Nature Chemistry; vol. 12; 3; (2020); p. 260 – 269;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles