Triethylamine → HCID 21075864, compound

HRID 1374159Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[C:15]2[N:16]=[N:17][N:18]([CH3:20])[N:19]=2)[CH:7]=1.[CH2:22]([N:24](CC)CC)C.C[Si](C#N)(C)C>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:22]#[N:24])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[C:15]2[N:16]=[N:17][N:18]([CH3:20])[N:19]=2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-chloro-5-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-pyridine 1-oxide (1.835 g, 5.983 mmol) and triethylamine (1.816 g, 17.95 mmol) in 10 mL DMF was added trimethylsilyl cyanide (1.781 g, 17.95 mmol). The reaction mixture was heated to 80° C. for 3 hours (added another 0.592 g, 2.98 mmol TMS-CN at this point and let stir another hour), then cooled to room temperature and partitioned between ethyl acetate and water. The organic extract was washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuum to provide crude 3-chloro-5-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-pyridine-2-carbonitrile that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 315.14 for M+H+. The 1H NMR also shows that the isomeric 5-chloro-3-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]pyridine-2-carbonitrile was present in about 20%. This would be separated out in a later step.

Workup

temperaturethen cooled to room temperature
custompartitioned between ethyl acetate and water
extractionThe organic extract
washwas washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-5f219fbabfe043b4812b5f15602e2017
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163951B2

Reaction notes

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