5-Aminoindole → (2E)-3-[6-(tert-Butyl)-2-methyl(3-pyridyl)]-N-indol-5-ylprop-2-enamide

HRID 730281Notes

Reaction equation

HRID 730281 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([CH3:11])[C:8](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2>>[C:1]([C:5]1[N:10]=[C:9]([CH3:11])[C:8](/[CH:12]=[CH:13]/[C:14]([NH:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][CH:22]=[CH:21]3)=[O:16])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 788675-AminoindoleHCID 57808155(2E)-3-[6-(1,1-Dimethylethyl)-2-methyl-3-pyridinyl]-2-propenoic acid

Product 1

HCID 10149894(2E)-3-[6-(tert-Butyl)-2-methyl(3-pyridyl)]-N-indol-5-ylprop-2-enamide

Procedure

Analogous to the procedure used to prepare Example 1, (2E)-3-[6-(tert-butyl)-2-methyl(3-pyridyl)]prop-2-enoic acid, Example 75(c), (0.88 g, 4.0 mmol) and 5-aminoindole (0.53 g, 4.0 mmol, Lancaster) provided, after purification by silica gel chromatography (55:45 hexane:EtOAc), the title compound as a yellow amorphous solid. MS (ESI, pos. ion) m/z: 334 (M+1).

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography (55:45 hexane:EtOAc)

Sources & evidence

ORD record
ord-3d378a8b23d749d59c9d436514555f6c
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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