Ethane, 1-fluoro-2-iodo- → HCID 86653735, compound

HRID 2088860Notes

Reaction equation

HRID 2088860 reaction equation
C([O-])(O)=O.[Na+].I[CH2:7][CH2:8][F:9].[I:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH:20][CH2:21][C@H:22]2[CH2:26][CH2:25][CH2:24][NH:23]2)=[O:19])=[CH:13][CH:12]=1>CN(C=O)C.O>[F:9][CH2:8][CH2:7][N:23]1[CH2:24][CH2:25][CH2:26][C@@H:22]1[CH2:21][NH:20][C:18](=[O:19])[CH2:17][C:14]1[CH:13]=[CH:12][C:11]([I:10])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 69804Ethane, 1-fluoro-2-iodo-HCID 516892Sodium BicarbonateHCID 67166754HCID 67166754, compound

Product 1

HCID 86653735HCID 86653735, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In a sealed tube, 0.53 g of NaHCO3 (6.4 mmol) and 0.49 g of 1-iodo-2-fluoroethane (2.8 mmol) are added to 0.88 g (2.6 mmol) of the compound obtained from step 1.10 dissolved in DMF (6 ml). The sealed tube is heated at 90° C. for 5 hours. The reaction mixture is cooled, the DMF is then evaporated off under reduced pressure, and the residue obtained is taken up in water (10 ml) and extracted with ethyl acetate (20 ml×2). The organic phase is dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue obtained is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol, 1% NH4OH), with a gradient of 0% to 10% methanol. 0.82 g of compound is obtained, in the form of a beige-coloured powder. Yield=85%. Melting point: 96° C. MH+: 391 (tr: 5.1 min., condition 1)

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe DMF is then evaporated off under reduced pressure
  3. customthe residue obtained
  4. extractionextracted with ethyl acetate (20 ml×2)
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue obtained
  9. customis purified by flash chromatography on silica gel (eluent: dichloromethane/methanol, 1% NH4OH), with a gradient of 0% to 10% methanol

Sources & evidence

ORD record
ord-8c1de9e619a84381b2fafdb7776d3b33
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

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