Sodium Iodide → (4-Chloro-5-iodo-pyridin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 74599Notes

Reaction equation

HRID 74599 reaction equation
[I-:1].[Na+].Br[C:4]1[C:5]([Cl:22])=[CH:6][C:7]([C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])=[N:8][CH:9]=1>O1CCOCC1.O.[Cu](I)I>[Cl:22][C:5]1[C:4]([I:1])=[CH:9][N:8]=[C:7]([C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=1

Participants

6

Reactant 2

HCID 5238Sodium IodideHCID 58386444(5-Bromo-4-chloro-pyridin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Product 1

HCID 58386447(4-Chloro-5-iodo-pyridin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Under a nitrogen atmosphere 1.3 g (8.4 mmol) sodium iodide, 80 mg (0.42 mmol) copper iodide and 90 μL (0.84 mmol) N,N-dimethylene-ethylenediamine were added to 1.5 g (4.2 mmol) (5-bromo-4-chloro-pyridin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone in 15 mL 1,4-dioxane and the mixture was stirred for 5 days at 110° C. The reaction mixture was diluted with water, the precipitate formed was suction filtered and dried.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-1526b83cc9854fb8bcc22f67b7bac1f9
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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