Water → 5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

HRID 1878637Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][N:8]([S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Add, at 0° C., 1 g of 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde, then 0.27 g of sodium hydride to 10 cm3 of anhydrous tetrahydrofuran. Stir the reaction mixture for fifteen minutes at 0° C. before adding 1.87 g of tosyl chloride in solution in 1.7 cm3 of tetrahydrofuran. Continue stirring the reaction mixture for two hours, allowing it to return to room temperature. Pour the reaction mixture into 100 cm3 of iced water. Extract the mixture obtained with two times 100 cm3 of ethyl acetate. Dry the organic phases over magnesium sulphate and then evaporate to dryness under vacuum in a rotary evaporator. 1.32 g of 5-bromo-1-[(4-methylphenyl)sulphonyl]-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde is obtained in the form of a beige powder with the following physical characteristics:

Workup

additionAdd, at 0° C.
stirringContinue stirring the reaction mixture for two hours
customto return to room temperature
extractionExtract the mixture
customobtained with two times 100 cm3 of ethyl acetate
dry with materialDry the organic phases over magnesium sulphate
customevaporate to dryness under vacuum in a rotary evaporator

Sources & evidence

ORD record: ord-2c912a36d7ce4df1b9634f472466c855
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314121B2

Reaction notes

Loading…