Water → HCID 66738229, compound

HRID 1640892Notes

Reaction equation

HRID 1640892 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29].O>CN(C=O)C>[F:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][N:19]2[C:20](=[O:29])[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]2=[O:28])=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 666745926-Fluoro-4-iodopyridin-3-ol

Product 1

HCID 66738229HCID 66738229, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cool a suspension of 6-fluoro-4-iodo-pyridin-3-ol (1.5 g, 6.28 mmol) and K2CO3 (4.38 g, 31.4 mmol) in DMF (10 mL) to 0° C. in an ice bath under nitrogen. Add 2-(2-bromo-ethyl)-isoindole-1,3-dione (3.19 g, 12.55 mmol). Stir the mixture at RT overnight. Add water. Extract with ethyl acetate. Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (hexane to 30% ethyl acetate in hexane) to afford the title compound as a yellow oil (1.51 g, 58%). MS (ES) m/z 413 [M+1]+.

Workup

  1. temperatureCool
  2. extractionExtract with ethyl acetate
  3. washWash the solution with aqueous saturated sodium chloride
  4. dry with materialDry over sodium sulfate
  5. concentrationConcentrate the solution in vacuo
  6. customPurify by column chromatography (hexane to 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2704b41511da4a2e8375717f165846b2
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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