Ethyl Bromide → 1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1622885Notes

Reaction equation

[F:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH3:18]>CN(C=O)C>[CH2:17]([N:8]1[C:6]2=[N:7][C:2]([F:1])=[CH:3][CH:4]=[C:5]2[CH:10]=[CH:9]1)[CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 6-fluoro-1H-pyrrolo[2,3-b]pyridine (15.00 g, 110.19 mmol) in DMF (100 mL), under a nitrogen atmosphere, is added potassium carbonate (22.84 g, 165.3 mmol), followed by ethyl bromide (12.36 mL, 165.3 mmol). The reaction is heated to 70° C. for 4 h. Further ethyl bromide (3.00 mL, 27.6 mmol) is added and the reaction kept at 70° C. overnight. After cooling further potassium carbonate (8.00 g, 57.9 mmol) and ethyl bromide (3.00 mL, 27.6 mmol) are added, and the reaction heated at 70° C. for 4 h. The reaction is cooled, poured onto brine (ca. 500 mL) and the product extracted with CHCl3 (ca. 2×300 mL). The combined organic extracts are dried over magnesium sulphate, filtered, and concentrated in vacuo to give a brown oil. This is purified by column chromatography on silica, eluting with 0 to 70% DCM in hexane to give the title compound as a light yellow oil (16.38 g, 99.77 mmol). MS (m/z): 165 (M+1).

Workup

additionare added
temperaturethe reaction heated at 70° C. for 4 h
temperatureThe reaction is cooled
additionpoured onto brine (ca. 500 mL)
extractionthe product extracted with CHCl3 (ca. 2×300 mL)
dry with materialThe combined organic extracts are dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a brown oil
customThis is purified by column chromatography on silica
washeluting with 0 to 70% DCM in hexane

Sources & evidence

ORD record: ord-04a9ce6b16c54b47a82d3a32d6bda3f6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778946B2

Reaction notes

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