Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1) → 3-fluoro-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2101957Notes

Reaction equation

HRID 2101957 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]([F:14])([F:13])[F:12])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2.[O-]S(C(F)(F)[F:22])(=O)=O.F[N+]1C=CC=CC=1>C(Cl)Cl>[F:22][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]#[N:16])[C:8]=2[C:11]([F:12])([F:14])[F:13])[NH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)HCID 533093462-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 578003103-fluoro-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrileYield 22.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.063 g, 0.28 mmol) in CH2Cl2 (4 mL) was added 1-fluoropyridinium triflate (0.104 g, 0.42 mmol) and stirred at rt for 3 days. The mixture was partitioned between EtOAc and 0.1N HCl. The organic phase was washed with 0.1N HCl and sat'd brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (10-50% EtOAc-hexanes gradient) to afford the title compound as a white solid (0.015 g, 22% yield, 94% purity): MS (ES) m/z 243 (M+1).

Workup

  1. customThe mixture was partitioned between EtOAc and 0.1N HCl
  2. washThe organic phase was washed with 0.1N HCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (10-50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-6e71cee8b8a94238912e302e8db185f8
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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