Water → 2-(pyridin-2-yl)-1H-indol-5-amine

HRID 468379Notes

Reaction equation

HRID 468379 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:7]2)([O-])=O.Cl[Sn]Cl.O>CCO>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 591293805-nitro-2-(pyridin-2-yl)-1H-indole

Product 1

HCID 591292842-(pyridin-2-yl)-1H-indol-5-amineYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-nitro-2-(pyridin-2-yl)-1H-indole (700 mg, 2.9 mmol) in EtOH (20 mL) was added SnCl2 (2.6 g, 12 mmol). The mixture was heated at reflux for 10 h. Water was added and the mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether) to afford 2-(pyridin-2-yl)-1H-indol-5-amine (120 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 9.33 (brs, 1H), 8.55 (dd, J=1.2, 3.6 Hz, 1H), 7.76-7.67 (m, 2H), 7.23 (d, J=6.4 Hz, 1H), 7.16-7.12 (m, 1H), 6.94 (d, J=2.0 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.71-6.69 (dd, J=2.0, 8.4 Hz, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 h
  3. extractionthe mixture was extracted with EtOAc (50 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-5cfaaa8266604a7e9e8a8b177c120494
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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