Isopropyl iodide → HCID 66920857, compound

HRID 1364535Notes

Reaction equation

HRID 1364535 reaction equation
[Na].[CH3:2][O:3][CH:4]([O:16][CH3:17])[C:5]1[CH:12]=[C:11]([S:13][CH3:14])[C:8]([C:9]#[N:10])=[C:7]([OH:15])[N:6]=1.I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[CH3:17][O:16][CH:4]([O:3][CH3:2])[C:5]1[CH:12]=[C:11]([S:13][CH3:14])[C:8]([C:9]#[N:10])=[C:7]([O:15][CH:19]([CH3:21])[CH3:20])[N:6]=1

Participants

4

Reactant 2

HCID 6362Isopropyl iodideHCID 178499540HCID 178499540, compound

Product 1

HCID 66920857HCID 66920857, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

6-Dimethoxymethyl-2-hydroxy-4-methylsulfanyl-nicotinonitrile sodium salt synthesized as described by Mahata, P. K. et al. Tetrahedron 59, 2003, 2631-2639 (3.5 g, 13.3 mmol) in 40 mL of anhydrous DMF was heated at 120° C. while 2-iodopropane (1.6 mL, 16.0 mmol) was added dropwise. The resulting mixture was heated at 120° C. for another 30 min before it was cooled to ambient temperature and partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, evaporated in vacuo. Purification on an Analogix MPLC system (SiO2 column) eluting with 10% EtOAc in hexanes yielded the titled compound as a light yellow solid upon standing (3.0 g, 80% yield).

Workup

  1. additionwas added dropwise
  2. temperaturewas cooled to ambient temperature
  3. custompartitioned between water and EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customPurification on an Analogix MPLC system (SiO2 column)
  8. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-e29aef6373024276a2764f45d8ea8424
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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