Trifluoroacetic acid → 2-(1H-Indol-3-yl)quinoline-4-carboxylic acid

HRID 1871602Notes

Reaction equation

HRID 1871602 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[CH:19]=[C:18]([C:20]([O-:22])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22616997HCID 22616997, compound

Product 1

HCID 226169942-(1H-Indol-3-yl)quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 3 mL plastic tube fitted with a frit containing 50 mg of resin-bound 2-(3-indolyl)quinoline-4-carboxylate (0.035 mmol) was added 1 mL of a 50% mixture of TFA and DCM. The reaction mixture was agitated on an orbital shaker for 30 min. The mixture was filtered and the resin washed with DCM (3×3 mL). The organic solutions were combined and evaporated by a stream of nitrogen. The residual solid was lyophilized to give 2-(3-indolyl)quinoline-4-carboxylic acid or amide (80-100% yield).

Workup

  1. customTo a 3 mL plastic tube fitted with a frit
  2. filtrationThe mixture was filtered
  3. washthe resin washed with DCM (3×3 mL)
  4. customevaporated by a stream of nitrogen

Sources & evidence

ORD record
ord-6923dbdc2cfe4c768a6a50f01fe2ffe4
Source dataset
uspto-grants-2000_08
Patent number
US06103905

Reaction notes

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