Ammonia → HCID 59332724, compound

Participants

Reaction Conditions

Reaction Steps

(racemic)-5-bromo-3-(1,1-dioxido-2,2-dimethylthian-4-yl)-1H-indole-7-carboxylic acid (490 mg, 1.224 mmol), was placed in a microwave flask and dissolved with DMF (2 mL) and 1,4-Dioxane (8 mL). HOBt (1-hydroxybenzotriazole) (165 mg, 1.224 mmol) and EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide) (657 mg, 3.43 mmol) was added. 0.5N NH3 in dioxane (7.34 mL, 3.67 mmol) was added. The reaction mixture was heated under microwave at 10° C. for 20 minutes. The reaction was diluted with saturated aqueous solution of sodium bicarbonate (20 mL) and extracted with ethyl acetate (2×). The organic layers were combined and washed with water, dried (MgSO4) and the solvent was removed under vacuum. The residue was dissolved in the minimum amount of EtOAc (around 2 mL, sonicating and heating when necessary), precipitated by adding hexane, and then filtering off the solid. This operation was repeated on the filtrate to increase the recovery affording a total of 332 mg of the title compound as a pale yellow powder.

Provenance & Evidence