Allyl iodide → HCID 68992981, compound

HRID 657054Notes

Reaction equation

HRID 657054 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9](=[O:11])[S:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH:19]=[CH2:20]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:20][CH:19]=[CH2:18])[C:9](=[O:11])[S:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 688162426-Fluoro[1,3]thiazolo[5,4-b]pyridin-2(1H)-one

Product 1

HCID 68992981HCID 68992981, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Fluoro[1,3]thiazolo[5,4-b]pyridin-2(1H)-one (0.045 g, 0.31 mmol) was dissolved in DMF (3 ml) and treated with potassium carbonate (0.043 g, 0.31 mmol) and allyl iodide (0.03 ml, 0.33 mmol) then heated at 100° C. for 18 hrs. The solvent was then removed in-vacuo and the residue partitioned between water and ethyl acetate. The organic layer was washed with saturated brine, separated and dried. Chromatography on silica gel eluting with a gradient of 10-50% ethyl acetate/40-60 petroleum ether gave the title compound (0.046 g, 83%) as an oil.

Workup

  1. customThe solvent was then removed in-vacuo
  2. customthe residue partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customseparated
  5. customdried

Sources & evidence

ORD record
ord-3a0faa37033f4ae8b2ac3ae93bdbc643
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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