4-(Trifluoromethoxy)aniline → Trifluoroacetic acid

HRID 1408476Notes

Reaction equation

HRID 1408476 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15](Cl)[C:10]=2[CH:9]=[CH:8]1)[CH3:2].[F:18][C:19]([F:29])([F:28])[O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>C(O)(CC)C>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:25][C:24]3[CH:26]=[CH:27][C:21]([O:20][C:19]([F:18])([F:28])[F:29])=[CH:22][CH:23]=3)[C:10]=2[CH:9]=[CH:8]1)[CH3:2].[C:4]([OH:17])([C:19]([F:18])([F:28])[F:29])=[O:3]

Participants

5

Reactant 2

HCID 6008484-(Trifluoromethoxy)anilineHCID 24974919HCID 24974919, compound

Product 2

HCID 6422Trifluoroacetic acidYield 540.4%HCID 68628504HCID 68628504, compound

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-propionic acid ethyl ester (100 mg, 0.37 mmol) in sec-BuOH (3 mL) was added 4-trifluoromethoxyaniline (73 mg, 0.41 mmol). The mixture was heated at 120° C. and stirred for 2 h. The reaction mixture was concentrated and purified by prep-HPLC to afford the title compound as brown solid as TFA salt (114 mg, 60%). MS m/z 408.1 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-89820e5c694444ca98c065e5319df18f
Source dataset
uspto-grants-2014_12
Patent number
US08921336B2

Reaction notes

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