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

HRID 730279Notes

Reaction equation

HRID 730279 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:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[CH:20][CH:19]=1>>[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:26]=[C:25]3[C:21]([CH:22]=[CH:23][NH:24]3)=[CH:20][CH:19]=2)=[O:16])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 2560966-AminoindoleHCID 57808155(2E)-3-[6-(1,1-Dimethylethyl)-2-methyl-3-pyridinyl]-2-propenoic acid

Product 1

HCID 10286636(2E)-3-[6-(tert-Butyl)-2-methyl(3-pyridyl)]-N-indol-6-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), (220 mg, 1.0 mmol) and 6-aminoindole (130 mg, 1.0 mmol, Lancaster) provided, after purification by silica gel chromatography (55:45 hexane:EtOAc), the title compound as a yellow solid. MP 182° C. 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-26f261e3a34c45bd9ba711dd79098055
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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