Pyridine → 3-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Pentafluorophenyl Ester

HRID 1376120Notes

Reaction equation

HRID 1376120 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([OH:19])=[O:18])=[CH:3][CH:2]=1.N1C=CC=CC=1.FC(F)(F)C(O[C:31]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41])=O>CN(C)C=O>[F:37][C:36]1[C:31]([O:18][C:17]([C:9]2[NH:10][C:11]3[C:16]([C:8]=2[NH:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:19])=[C:32]([F:41])[C:33]([F:40])=[C:34]([F:39])[C:35]=1[F:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 101989283-(pyridin-4-ylamino)-1H-indole-2-carboxylic Acid

Product 1

HCID 99794613-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Pentafluorophenyl EsterYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir under N2 a suspension of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid (0.2 g, 0.78 mmol) in dimethylformamide, add pyridine (0.13 mL, 1.6 mmol) and then add dropwise pentafluorophenyl trifluoroacetate (0.31 g, 1.13 mmol). Stir the reaction overnight at ambient temperature and quench into water. Extract the aqueous mixture with ethyl acetate, wash with 5% aqueous potassium carbonate, brine and dry over MgSO4. Concentrate under vacuum to afford a crude solid, which is triturated with ether to obtain 0.13 g (41%) of the title compound: MS 420(M+H).

Workup

  1. stirringStir
  2. customthe reaction overnight at ambient temperature
  3. customquench into water
  4. extractionExtract the aqueous mixture with ethyl acetate
  5. washwash with 5% aqueous potassium carbonate, brine
  6. dry with materialdry over MgSO4
  7. concentrationConcentrate under vacuum
  8. customto afford a crude solid, which
  9. customis triturated with ether

Sources & evidence

ORD record
ord-8fd45b7092a64aa4b22eccb752c5b292
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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