Trifluoroacetic acid → [1-(2-Ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic Acid

HRID 641406Notes

Reaction equation

HRID 641406 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH:11]=[CH:12][CH:13]=2)[C:8]([N+:23]([O-:25])=[O:24])=[CH:7]1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:12][CH:13]=2)[C:8]([N+:23]([O-:25])=[O:24])=[CH:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57426201tert-Butyl[1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetate

Product 1

HCID 57426202[1-(2-Ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetate from Step E (300 mg, 0.828 mmol) in CH2Cl2 (1 mL) was added TFA (0.63 mL, 8.28 mmol). The mixture was stirred at ambient temperature for 1 h then concentrated in vacuo to give the title compound. MS: m/z=307 (M+1).

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-cc2f41b788da49cebac35d8ad886390e
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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