Trifluoroacetic acid → HCID 67414256, compound

HRID 220615Notes

Reaction equation

HRID 220615 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16][C:17]#[N:18])=[O:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16][C:17]#[N:18])=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67415407HCID 67415407, compound

Product 1

HCID 67414256HCID 67414256, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.30 g (0.8 mmol) of 5-chloro-7-cyanomethyl-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in CH2Cl2 (8 ml) at RT was added 2 ml of TFA. The reaction mixture was stirred at RT for one hour and concentrated under vacuo. The crude was taken up in EtOAc and neutralized with aqueous NaHCO3. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Preparative HPLC (30% CH3CN/H2O) afforded 81 mg (35%) of 5-chloro-7-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. concentrationconcentrated under vacuo
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc28e54fc7534d7f854a4c75c8cba260
Source dataset
uspto-grants-2012_06
Patent number
US08202993B2

Reaction notes

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