3-(Trifluoromethyl)aniline → 1-(3-Thienyl)-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-one

HRID 252294Notes

Reaction equation

HRID 252294 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=O)[C:7]2=[O:16])=[CH:2]1.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22]>>[S:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[N:22][C:21]3[CH:23]=[CH:24][CH:25]=[C:19]([C:18]([F:17])([F:26])[F:27])[CH:20]=3)[C:7]2=[O:16])=[CH:2]1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 220224311-(3-Thienyl)-1H-indole-2,3-dione

Product 1

HCID 220224471-(3-Thienyl)-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-oneYield 22%

Conditions

Temperature
140 °C

Procedure

A mixture of 1-(3-thienyl)-2H-indole-2,3-dione (25 mg, 0.11 mmol) (prepared as described below) and 3-trifluoromethylaniline (14 uL, 0.11 mmol) was heated neat at 140° C. for 2 h. The crude material was purified by preparative TLC using a mixture of 3:7 ethyl acetate and hexane as the eluent, giving the desired product as a yellow solid (7.3 mg, 0.02 mmol, 22%). 1H NMR (400 MHz) δ 7.62-7.19 (m, 9H), 6.94 (d, J=8.0, 1H), 6.76 (t, J=7.6, 1H); ESI-MS m/z found 373 (MH+).

Workup

  1. customThe crude material was purified by preparative TLC
  2. additiona mixture of 3:7 ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-32508782d37148c88830af0caf086797
Source dataset
uspto-grants-2011_01
Patent number
US07868034B2

Reaction notes

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