Iodine → HCID 178521469, compound

HRID 1818745Notes

Reaction equation

HRID 1818745 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][NH:11]2)=[C:7]([O:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])[CH:6]=1.[OH-].[K+].[I:27]I>CN(C=O)C>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([I:27])=[N:10][NH:11]2)=[C:7]([O:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])[CH:6]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 68819211HCID 68819211, compound

Product 1

HCID 178521469HCID 178521469, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[6-(2,4-Difluoro-phenoxy)-1H-indazol-4-yloxy]-propane-1,2-diol (0.45 g, 1.34 mmol) was dissolved in 5 mL of dry DMF, and powdered KOH (0.288 g, 5.1 mmol) was added. The reaction mixture was stirred under nitrogen for 10 minutes at room temperature, and iodine (0.536 g, 2.11 mmol) was added in two portions. The reaction mixture was stirred for 90 minutes. The reaction mixture was partitioned between EtOAc and 5% aqueous sodium bisulfite solution, and the organic layer was separated, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed through silica (0%-5% MeOH in dichloromethane) to give 0.408 g of 3-[6-(2,4-difluoro-phenoxy)-3-iodo-1H-indazol-4-yloxy]-propane-1,2-diol, MS(M+H)=436.

Workup

  1. stirringThe reaction mixture was stirred for 90 minutes
  2. customThe reaction mixture was partitioned between EtOAc and 5% aqueous sodium bisulfite solution
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed through silica (0%-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-e1192f0abe9a4b7997ec0fa753197782
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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