1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59146118, compound

Participants

Reaction Steps

HOBT (216 mg) and EDCI (273 mg) were added to a solution of 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D32) (151 mg) in THF (4 mL). The reaction mixture was stirred at RT for 1 hour. Ethyl 3-{5-fluoro-7-[(Z)-(hydroxyamino)(imino)methyl]-1H-indol-3-yl}propanoate (D136) (268 mg) in THF (4 mL) was added. Then stirring continued overnight. TBAF (1.18 g) was then added. The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 120° C. for 1.5 hours. After cooling, the reaction was quenched with water, and extracted with EtOAc for 3 times. The combined organic solution was washed with brine, and dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography to afford ethyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoate (D137) (287 mg) as a pale yellow solid. MS (ES): C24H23ClFN3O4 requires 471; found 472.2 (M+H+).

Provenance & Evidence