Water → HCID 131734966, compound

Reaction equation

COCCC[N:6]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=[CH:10][C:9]=2[CH:8]=[CH:7]1.BrN1C(=O)CC[C:22]1=[O:27].O.Cl[CH2:30]Cl>>[CH3:30][O:27][CH2:22][CH2:19][CH2:18][O:17][C:15]([C:12]1[N:11]=[CH:10][C:9]2[CH:8]=[CH:7][NH:6][C:14]=2[CH:13]=1)=[O:16]

Participants

Reactant 4

HCID 962Water

HCID 6344Dichloromethane

HCID 67184N-bromobutanimide

HCID 89925499HCID 89925499, compound

Product 1

HCID 131734966HCID 131734966, compound

Procedure

To a solution of ethyl 1-(3-methoxypropyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (2.00 g) in dichloromethane (40 mL) was added N-bromosuccinimide (1.49 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the mixture was extracted with chloroform. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1) to give ethyl 3-bromo-1-(3-methoxypropyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate [REx(105-3)] (2.12 g) as a yellow oil.