Hydrochloric Acid → HCID 68284225, compound

Participants

Reaction Steps

5-Allyloxy-3-formyl-indole-1-carboxylic acid amide (530 mg, 2.17 mmol) was dissolved in a mixture of THF (38 mL) and t-butanol (12 mL). 2-methyl-2-butene 2 M solution in THF (40 mL, 80 mmol) was added, followed by a water (9.5 mL) solution of NaClO2 (80%, 2.45 g, 21.7 mmol) and NaH2PO4 (2.08 g, 17.4 mmol). The resulting solution was stirred at RT for 1 h, until consumption of the starting material. HCl 1N (3 mL) was added, and the organic solvents were concentrated. The remaining aqueous layer was filtered and the resulting precipitate was washed with water and Et2O to give the desired compound. TLC, Rf (c-hexane/EtOAc 1:2)=0.08; LC/MS: 261.1 [M+H]+, 259.0 [M−H]−, 216.1 [M−CONH2]−, 519.1 [2M−H]−; tR (HPLC conditions a): 2.8 min.

Provenance & Evidence