1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59452214, compound

Participants

Reaction Steps

EDCI (259 mg, 1.08 mmol) and HOBt (204 mg, 1.51 mmol) were added to a suspension of sodium 1-(2-fluoro-4-iodo-benzyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (494 mg, 1.08 mmol) in THF (7 ml). The suspension was warmed gently for 1 minute before the addition of a solution of O—((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine (222 mg, 1.51 mmol) in THF (3 ml) followed by DIPEA (0.19 ml, 1.10 mmol). The reaction mixture was stirred at room temperature for 18 hours, poured into ethyl acetate (60 ml) and washed sequentially with 0.1M HCl (10 ml), saturated NaHCO3 solution (10 ml) and brine (10 ml). The organic layer was isolated and dried over magnesium sulphate, then concentrated in vacuo to provide a residue. Trituration of the residue in dichloromethane afforded the title compound as a pale cream solid (0.433 g, 76%). LCMS (method B): RT=2.32 min, (M+H)+=524, M+H+=526.

Provenance & Evidence