3-(Trifluoromethyl)aniline → 1-[(5-Chloro-2-thienyl)methyl]-3-{[3-(trifluoromethyl)phenyl]imino}1,3-dihydro-2H-indol-2-one

HRID 1352914Notes

Reaction equation

HRID 1352914 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=O)[C:9]2=[O:18])=[CH:4][CH:3]=1.[F:19][C:20]([F:29])([F:28])[C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24]>>[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[N:24][C:23]3[CH:25]=[CH:26][CH:27]=[C:21]([C:20]([F:19])([F:28])[F:29])[CH:22]=3)[C:9]2=[O:18])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 220224391-(5-Chloro-thiophen-2-yl-methyl)-1h-indole-2,3-dione

Product 1

HCID 100707821-[(5-Chloro-2-thienyl)methyl]-3-{[3-(trifluoromethyl)phenyl]imino}1,3-dihydro-2H-indol-2-oneYield 61%

Conditions

Temperature
140 °C

Procedure

A mixture of 1-[(5-chloro-2-thienyl)methyl]-2H-indole-2,3-dione (25 mg, 0.09 mmol) (prepared as described below) and 3-trifluoromethylaniline (11.3 μL, 0.09 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 in hexane as the eluent, giving the desired product (23 mg 0.05 mmol, 61%). 1H NMR (400 MHz): δ (major isomer) 7.57 (t, J=7.7, 1H), 7.53 (t, J=7.8, 1H), 7.33 (t, J=7.8, 1H), 7.28 (s, 1H), 7.19 (d, J=7.6, 2H), 6.24-6.72 (m, 4H), 6.56 (d, J=7.7, 1H), 5.02 (s, 2H); ESI-MS m/z found 421 (MH+).

Workup

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

Sources & evidence

ORD record
ord-c5edbbbf587644af950fb978ee5f8d50
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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