5-Aminoindole → (2E)-3-[2-Bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide

HRID 2105594Notes

Reaction equation

HRID 2105594 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]([OH:16])=O.[NH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]([NH:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2)=[O:16]

Participants

3

Reactant 2

HCID 788675-AminoindoleHCID 578081432-Bromo-4-(trifluoromethyl)cinnamic acid

Product 1

HCID 57807978(2E)-3-[2-Bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide

Procedure

Analogous to the procedure used to prepare Example 1, (2E)-3-[2-bromo-4-(trifluoromethyl)phenyl]prop-2-enoic acid, Example 97(e), (140 mg, 0.48 mmol) and 5-aminoindole (75 mg, 0.57 mmol, Aldrich) provided, after purification by silica gel chromatography (gradient: 0-25% EtOAc in hexane), the title compound as a yellow solid. MP 205-207° C. MS (ESI, pos. ion) m/z: 409 (M+1).

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography (gradient: 0-25% EtOAc in hexane)

Sources & evidence

ORD record
ord-10f2fc530800485f8581a5c382a40bbd
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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