Trifluoroacetic acid → HCID 67414256, compound

HRID 912749Notes

Reaction equation

HRID 912749 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-0e96e1fba3ae41fcbc7a5edc4cc2ded7
Source dataset
uspto-grants-2011_09
Patent number
US08026259B2

Reaction notes

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