Water → HCID 66738538, compound

HRID 1640896Notes

Reaction equation

HRID 1640896 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.[O:10]=[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:12]1[CH:21]([CH3:34])[CH2:22]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:34][CH:21]([N:12]2[C:13](=[O:20])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]2=[O:10])[CH3:22])=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 13477640HCID 13477640, compoundHCID 666745926-Fluoro-4-iodopyridin-3-ol

Product 1

HCID 66738538HCID 66738538, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat a mixture of 6-fluoro-4-iodo-pyridin-3-ol (150 mg, 0.63 mmol), toluene-4-sulfonic acid 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl ester (226 mg, 0.63 mmol), cesium carbonate (206 mg, 0.63 mmol) in DMF (2 mL) at 100° C. for 5 h. Cool the mixture and add water. Extract with ethyl acetate. Wash the organic layer with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to a light yellow solid. Purify by column chromatography (hexane to 10% ethyl acetate in hexane) to afford the title compound as a white solid (115 mg, 43%). MS (ES) m/z 427 [M+1]+.

Workup

  1. temperatureHeat
  2. temperatureCool the mixture
  3. extractionExtract with ethyl acetate
  4. washWash the organic layer with aqueous saturated sodium chloride
  5. dry with materialDry over sodium sulfate
  6. concentrationConcentrate the solution in vacuo to a light yellow solid
  7. customPurify by column chromatography (hexane to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5fdfebc12d2e48ceb52259a34b971b22
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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