4-Aminoindole → HCID 49784797, compound

HRID 1811901Notes

Reaction equation

HRID 1811901 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:9]=1.[NH2:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2>CCO.C([O-])(O)=O.[Na+]>[NH:24]1[C:25]2[C:21](=[C:20]([NH:19][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[C:8]3[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:9]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1.[NH2:15][C:10]1[N:11]=[C:12]([CH3:14])[N:13]=[C:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[NH:19][C:20]2[C:21]3[CH:22]=[CH:23][NH:24][C:25]=3[CH:26]=[CH:27][CH:28]=2)[CH:9]=1

Participants

6

Reactant 2

HCID 5834314-AminoindoleHCID 68517076HCID 68517076, compound

Product 2

HCID 49784796HCID 49784796, compoundYield 35%HCID 49784797HCID 49784797, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of N-(6-(4-chloropyridin-3-yl)-2-methylpyrimidin-4-yl)acetamide (50 mg, 190 μmol) and 4-aminoindole (50 mg, 381 μmol, Alfa Aesar) in EtOH (2 mL) was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 160° C. for 30 min. The reaction mixture was diluted with saturated NaHCO3 (3 mL) and extracted with EtOAc (3×20 mL). The organic extract was washed with saturated NaCl (2 mL), dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel chromatography eluting with 10% MeOH/EtOAc to give N-(6-(4-(1H-indol-4-ylamino)pyridin-3-yl)-2-methylpyrimidin-4-yl)acetamide (24 mg, 35% yield) and N-(3-(6-amino-2-methylpyrimidin-4-yl)pyridin-4-yl)-1H-indol-4-amine (22 mg, 37% yield).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaCl (2 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-aa477b17971541f3ab5806d12b89706b
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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