Sodium Iodide → 4-Iodo-1-(4-fluorophenyl)indazole

HRID 1661449Notes

Reaction equation

HRID 1661449 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.[I-:18].[Na+].CNC1CCCCC1NC>O1CCOCC1.[Cu]I>[I:18][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 666871004-Bromo-1-(4-fluorophenyl)-1H-indazole

Product 1

HCID 666878174-Iodo-1-(4-fluorophenyl)indazoleYield 98%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

4-Bromo-1-(4-fluorophenyl)indazole (291 mg, 1 mmol), copper(I)iodide (9.5 mg, 0.05 mmol), sodium iodide (300 mg, 2 mmol) and (1R,2R)—(N,N′-dimethylcyclohexane-1,2-diamine (14.2 mg, 0.1 mmol) in dioxane (1 ml) were mixed and stirred in argon at 110° C. All starting material was consumed after 24 h. The mixture was cooled and ammonia (5 ml, 28% in water) and water (20 ml) were added followed by extraction with DCM (2×15 ml). The organic phase was concentrated and the crude product was purified by flash chromatography (EtOAc/Heptane) to give the title compound (322 mg, 98%).

Workup

  1. customwas consumed after 24 h
  2. temperatureThe mixture was cooled
  3. additionammonia (5 ml, 28% in water) and water (20 ml) were added
  4. extractionfollowed by extraction with DCM (2×15 ml)
  5. concentrationThe organic phase was concentrated
  6. customthe crude product was purified by flash chromatography (EtOAc/Heptane)

Sources & evidence

ORD record
ord-c8f3d2efad864d6685702790564b0b14
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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