Bromine → Benzyl 3-bromo-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

HRID 887362Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyl 1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate (9.48 g, 35.5 mmol) in chloroform (100 mL) was cooled to 5° C. and treated dropwise with bromine (1.86 mL, 36.21 mmol, 1.02 Eq). The reaction was allowed to to stir at 0° C. for 1 hour and then at room temperature for 1 hour. The mixture was diluted with DCM and washed with a 1:1 sat. aq. sodium thiosulfate/sodium bicarbonate solution (200 mL). The organic layer was separated and the aqueous layer taken to pH 12 and re-extracted with EtOAc. The combined organics were dried over magnesium sulphate, filtered and dried under vacuum and the resultant brown solid triturated with diethyl ether/EtOAc to give 10.24 g (83%) of the title compound.

Workup

waitat room temperature for 1 hour
washwashed with a 1:1 sat. aq. sodium thiosulfate/sodium bicarbonate solution (200 mL)
customThe organic layer was separated
extractionre-extracted with EtOAc
dry with materialThe combined organics were dried over magnesium sulphate
filtrationfiltered
customdried under vacuum
customthe resultant brown solid triturated with diethyl ether/EtOAc

Sources & evidence

ORD record: ord-0fe51fc235be47cc9929178a21fb90ff
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247421B2

Reaction notes

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