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

HRID 2426201Notes

Reaction equation

HRID 2426201 reaction equation
C([O:5][C:6](=[O:26])[CH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([N+:23]([O-:25])=[O:24])=[CH:11][N:12]2[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:12]1[C:13]2[C:9](=[C:8]([CH2:7][C:6]([OH:26])=[O:5])[CH:16]=[CH:15][CH:14]=2)[C:10]([N+:23]([O-:25])=[O:24])=[CH:11]1)[CH3:22]

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-4bc0b27ab17a4bff8e8ccf7b2681e84b
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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