Iodine → HCID 178505575, compound

HRID 508199Notes

Reaction equation

HRID 508199 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[I:11]I.[OH-].[K+].OS([O-])=O.[Na+]>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([I:11])=[N:5][NH:6]2

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 224777574-Fluoro-1H-indazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178505575HCID 178505575, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoroindazole A-1 (5.00 g, 36.7 mmol) in DMF (80 mL) was added I2 (18.6 g, 73.5 mmol) and KOH (7.73 g, 134 mmol) successively at rt. After 2 h, the reaction mixture was poured into aq. 10% NaHSO3 (200 mL) and extracted with EtOAc (200 mL*3). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated. The crude solid was washed with PE to give the title compound as a yellow solid. LCMS (ESI) calc'd for C7H5FIN2 [M+H]+: 262.9. found: 262.9.

Workup

  1. extractionextracted with EtOAc (200 mL*3)
  2. washThe combined organic layers were washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. washThe crude solid was washed with PE

Sources & evidence

ORD record
ord-49074fa8be124542bda055eb954d009f
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

Loading…