Diisopropylethylamine → HCID 11647352, compound

Participants

Reaction Steps

1-Methyl-7-(pyridine-4-yloxy)-1H-indole-2-carboxylic acid (145 mg, 0.542 mmol) and HATU (206 mg, 0.542 mmol) were combined in DMF (1 mL) and stirred 5 min at room temperature. The above aminopyridinone (90 mg, 0.542 mmol) was added to the reaction mixture followed by N,N-diisopropylethylamine (283 microL, 1.63 mmol). The solution was stirred at room temperature for 72 h then poured into saturated aqueous NaHCO3. The aqueous layer was extracted with chloroform and the combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica-gel chromatography (2% ammonium hydroxide, 50% ethyl acetate in hexane) provided 1-methyl-7-(pyridine-4-yloxy)-1H-indole-2-carboxylic acid (5-tert-butyl-2-oxo-1,2-dihydropyridin-3-yl)-amide (163 mg, 73%) as a white solid: mp: 236-238° C. (dec.); ESI MS m/z 417 [C24H24N4O3+H]+; HPLC>97%, tR=14.74 min.

Provenance & Evidence