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

HRID 913523Notes

Reaction equation

HRID 913523 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-a8864ad720984882b6b423efc4a26f5d
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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