Water → 5-Bromo-1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

HRID 1804753Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[CH2:12][CH2:11][NH:10][C:7]2=[N:8][CH:9]=1.[CH3:13]I.O>CN(C)C=O.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[CH2:12][CH2:11][N:10]([CH3:13])[C:7]2=[N:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension stirred at 0° C., under an inert atmosphere, of 0.48 g (12.06 mmol) of 60% sodium hydride in 5 mL of dimethylformamide is added dropwise a solution of 5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine in 10 mL of dimethylformamide. The mixture is stirred at 0° C. for 15 minutes and then at 20° C. for 45 minutes. A solution of 0.77 mL (12.06 mmol) of methyl iodide in 5 mL of dimethylformamide is then added to this stirred suspension at 0° C. The mixture is then stirred for 48 hours. After this time, 50 mL of water and 50 mL of ethyl acetate are added to the mixture. The aqueous phase is separated out and then extracted with 3×30 mL of ethyl acetate. The organic phases are combined, washed with 2×50 mL of water and then concentrated under reduced pressure. The resulting product is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol. 0.97 g of the expected product is thus isolated.

Workup

waitat 20° C. for 45 minutes
stirringThe mixture is then stirred for 48 hours
customThe aqueous phase is separated out
extractionextracted with 3×30 mL of ethyl acetate
washwashed with 2×50 mL of water
concentrationconcentrated under reduced pressure
customThe resulting product is purified by chromatography on a column of silica
washeluting with a mixture of dichloromethane and methanol

Sources & evidence

ORD record: ord-5173dcd9f77049799a8d9b1b2ac6a774
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354425B2

Reaction notes

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