Tetrabutylammonium Fluoride → 5-chloro-4-(trifluoromethyl)-1H-indole

HRID 1188362Notes

Reaction equation

HRID 1188362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C(C)(C)C)=[C:4]([C:15]#[C:16][Si](C)(C)C)[C:3]=1[C:21]([F:24])([F:23])[F:22].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][CH:16]=[CH:15]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57800198HCID 57800198, compound

Product 1

HCID 578001415-chloro-4-(trifluoromethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-{4-chloro-3-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]phenyl}-2,2-dimethylpropanamide (Example 60B) in THF (10 mL) was treated with TBAF (3.2 mL, 1 M in THF, 3 equiv) and the reaction mixture was left to stir at ambient temperature for 14 h. Concentration was followed by partitioning between EtOAc and water. The organic portion was dried (Na2SO4), filtered, and concentrated to a waxy yellow solid. This material was used for the next reaction without further purification: MS (ESI): m/z 218 (M−1).

Workup

  1. waitthe reaction mixture was left
  2. concentrationConcentration
  3. customby partitioning between EtOAc and water
  4. dry with materialThe organic portion was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a waxy yellow solid
  7. customThis material was used for the next reaction without further purification

Sources & evidence

ORD record
ord-32ad9613b94a46b8bf6d2084df854627
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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