Triethylamine → HCID 68516952, compound

HRID 1948363Notes

Reaction equation

HRID 1948363 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[N+:5]([O-])=[CH:6][CH:7]=1.C[CH2:16][N:17](CC)CC.C[Si](C#N)(C)C>CC#N.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:16]#[N:17])[N:5]=[C:4]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 68517369HCID 68517369, compound2×

Product 1

HCID 68516952HCID 68516952, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 200 mg (0.86 mmol) of isopropyl 4-chloropyridine-2-carboxylate 1-oxide (Intermediate 223), 0.14 ml (1 mmol) Et3N and 0.36 ml (2.7 mmol) of trimethylsilylcyanide in 3 ml CH3CN was heated at 90° C. overnight. The solution was diluted with EtOAc and washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil that was purified by chromatography on silica gel (100% CH2Cl2 followed by gradient elution to 10% EtOAc in CH2Cl2) to afford 130 mg of product as a white solid. MS (ES) (MH+): 224 for C19H9ClN2O2; NMR (d6-DMSO): 1.35 (d, 6H), 5.2 (septet, 1H), 8.4 (s, 1H), 8.6 (s, 1H).

Workup

  1. washwashed with water and brine
  2. customDrying
  3. custom(MgSO4) and removal of solvent
  4. customgave an oil that
  5. customwas purified by chromatography on silica gel (100% CH2Cl2 followed by gradient elution to 10% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-c5b4cd1d5eef411f8536d9a37e99915a
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…