Triethylamine → 5-(Benzyloxy)-3-bromopicolinonitrile

HRID 340222

Reaction equation

HRID 340222 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N+:11]([O-])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:21]#[N:22])(C)C.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:15])[C:12]([C:21]#[N:22])=[N:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 582134893-(benzyloxy)-5-bromopyridine N-oxide

Product 1

HCID 671177075-(Benzyloxy)-3-bromopicolinonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 53-(benzyloxy)-5-bromopyridine 1-oxide (from step 2) (1.0 eq.) in acetonitrile (0.2 M) was added trimethylsilyl cyanide (TMSCN) (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100° C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-40% ethyl acetate in hexane to give a mixture of two benzoxy regioisomers, one of which was the desired product. The mixture was carried onto the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solvent was concentrated en vacuo
  3. customthe residue was purified by a COMBIFLASH® system (ISCO)
  4. customto give
  5. additiona mixture of two benzoxy regioisomers, one of which

Sources & evidence

ORD record
ord-79c3e6c71bb74976b38875d78721c99b
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Linked notes

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