Water → methyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 550899Notes

Reaction equation

Cl.[NH:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[CH:4]=[C:3]1[C:11]([O:13][CH3:14])=[O:12].[Br-:15].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>N1C=CC=CC=1>[Br:15][C:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[NH:2][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3.2 g of methyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate hydrochloride in 165 mL of pyridine is added dropwise, at 0° C. under an argon atmosphere, a solution of 5.04 g of pyridinium tribromide in 35 mL of pyridine. The reaction mixture is then stirred at 0° C., and then poured onto a mixture of 250 g of crushed ice and 750 ml of distilled water. The suspension is filtered and the solid is washed with twice 25 mL of distilled water and then dried in the open air. 0.87 g of methyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate is obtained in the form of a beige-coloured solid, the characteristics of which are as follows:

Workup

filtrationThe suspension is filtered
washthe solid is washed with twice 25 mL of distilled water
customdried in the open air

Sources & evidence

ORD record: ord-f666b633612348f681c3270f17bb3df6
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947706B2

Reaction notes

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