Acetonitrile → HCID 89536561, compound

HRID 340451Notes

Reaction equation

HRID 340451 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.C(#N)C.[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([S:35]([C:38]1[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[C:30]([Sn](C)(C)C)=[CH:29]2>C(Cl)(Cl)Cl>[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([S:35]([C:38]1[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[C:30]([F:21])=[CH:29]2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2724933SelectfluorHCID 89537885HCID 89537885, compound

Product 1

HCID 89536561HCID 89536561, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-fluoro-N′-(chloromethyl)triethylenediamine bis(tetrafluoroborate) (2.33 g) was added to an acetonitrile solution (88 ml) containing 5-chloro-1-tosyl-2-(trimethylstannyl)-1H-indole (2.05 g) obtained in the 2nd step in a nitrogen atmosphere, followed by stirring at room temperature for 16 hours. Chloroform was added to the reaction solution, an insoluble precipitate was removed, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=0:1 to 1:100), and a light yellow solid of 5-chloro-2-fluoro-1-tosyl-1H-indole (520 mg) was thus obtained.

Workup

  1. customobtained in the 2nd step in a nitrogen atmosphere
  2. customan insoluble precipitate was removed
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=0:1 to 1:100)

Sources & evidence

ORD record
ord-e22518ad8da34c789fe7bc3f53c7095d
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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