Copper-Catalyzed N-Alkynylation of N-tert-Butoxycarbonyl (BOC)-Protected Indoles was written by Song, Jiahui;Wang, Qingbo;Fu, Haixing;Fu, Songlin;Li, Shaobin;Shi, Feng;Wu, Chunrui. And the article was included in Asian Journal of Organic Chemistry in 2013.Computed Properties of C20H28BNO5 This article mentions the following:
N-BOC-indole derivatives undergo a copper-catalyzed N-alkynylation with alkynyl bromides after in situ deprotection. Potassium tert-butoxide was used for the deprotection of substrates and as a base during the cross-coupling stage. For substrates that contain a 2-pyridine group or similar group, a phenanthroline ligand was not needed. This serves as an alternative protocol for N-alkynylation of indoles with a broader scope of substrates. The title compounds thus formed included an (ethynyl)indole derivative (I) and related substances. The synthesis of the target compounds was achieved using 3-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 5-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 1H-Indole-1,2-dicarboxylic acid 1,2-bis(1,1-dimethylethyl) ester, 4-cyano-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, etc., as starting materials in a reaction with bromoalkyne derivatives A similar reaction of 1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester gave 1-(2-phenylethynyl)-1H-benzimidazole. A reaction of 1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester derivatives gave 1-(2-phenylethynyl)-1H-pyrrole derivatives In the experiment, the researchers used many compounds, for example, tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5Computed Properties of C20H28BNO5).
tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C20H28BNO5
Referemce:
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