Bromine → 3-Bromo-4-nitro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine

HRID 2240226Notes

Reaction equation

[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:7]=12)([O-:5])=[O:4]>ClCCl>[Br:1][C:14]1[C:7]2[C:8](=[N:9][CH:10]=[CH:11][C:6]=2[N+:3]([O-:5])=[O:4])[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., 18 μl (6.13 mmol) of bromine are added dropwise to a solution of 100 mg (340 μmol) of 4-nitro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine in 10 ml of dichloromethane. After 1 h of stirring at 0° C. and 1 h of stirring at RT, the reaction solution is filtered through an Extrelut silica gel cartridge, the cartridge is washed with a little dichloromethane/methanol and the filtrate is concentrated under reduced pressure. The residue is purified by preparative RP-HPLC.

Workup

stirringof stirring at RT
filtrationthe reaction solution is filtered through an Extrelut silica gel cartridge
washthe cartridge is washed with a little dichloromethane/methanol
concentrationthe filtrate is concentrated under reduced pressure
customThe residue is purified by preparative RP-HPLC

Sources & evidence

ORD record: ord-7459c99627cf4eb094867847f13a2da3
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723347B2

Reaction notes

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