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Triethylamine → HCID 21075864, compound

HRID 1374159
Notes
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Reaction equation

HRID 1374159 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanide2×HCID 21075863HCID 21075863, compound

Product 1

HCID 21075864HCID 21075864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperaturethen cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes