Potassium Carbonate → N-{5-[(1S)-1-azidoethyl]pyridin-3-yl}-3-methylbenzamide

HRID 1255841Notes

Reaction equation

[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH2:9])=[O:8])[CH:2]=1.[N:11]([C@H:14]([C:16]1[CH:17]=[N:18][CH:19]=[C:20](Br)[CH:21]=1)[CH3:15])=[N+:12]=[N-:13].CN(C)CCN.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[N:11]([C@H:14]([C:16]1[CH:21]=[C:20]([NH:9][C:7](=[O:8])[C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=2)[CH:19]=[N:18][CH:17]=1)[CH3:15])=[N+:12]=[N-:13]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of m-toluamide (164 mg, 1.21 mmol), 3-[(1S)-1-azidoethyl]-5-bromopyridine (227 mg, 1 mmol), copper (I) iodide (9.6 mg, 0.05 mmol), N,N-dimethylethylene diamine (0.011 mL, 0.1 mmol) and potassium carbonate (276 mg, 2 mmol) in dioxane (1 mL) was heated in a microwave reactor at 110° C. for 30 minutes then at 160° C. for a further 30 minutes. After this time the mixture was allowed to cool to room temperature, was diluted with ethyl acetate (5 mL) and was filtered through Celite. The filtrate was concentrated under reduced pressure to give a brown oil which was purified by flash chromatography (silica, ethyl acetate/dichloromethane) to give N-{5-[(1S)-1-azidoethyl]pyridin-3-yl}-3-methylbenzamide (80 mg, 28%) as a colourless oil.

Workup

temperatureto cool to room temperature
filtrationwas filtered through Celite
concentrationThe filtrate was concentrated under reduced pressure
customto give a brown oil which
customwas purified by flash chromatography (silica, ethyl acetate/dichloromethane)

Sources & evidence

ORD record: ord-943bdd80a1cf44b39ee5dad24f7fbcf5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461161B2

Reaction notes

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