HCID 17810719, compound → HCID 17810717, compound

HRID 348512Notes

Reaction equation

HRID 348512 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)=[CH:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])=[CH:3]1

Participants

5

Reactant 2

HCID 17810719HCID 17810719, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17810717HCID 17810717, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

829 mg (6 mmol) of 2-nitroaniline and 1242 mg (7.8 mmol) of 1-methylindole carboxyaldehyde were dissolved in 20 ml of tetrahydrofuran followed by the sequential addition of 200 μl of acetic acid and 5087 mg (24 mmol) of NaBH(OAc)3 and stirring overnight at room temperature. After adding saturated aqueous sodium bicarbonate solution, extracting with ethyl acetate and drying with anhydrous magnesium sulfate, the solvent was distilled off and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5) to obtain 264 mg of ((1-methylindole-3-yl)methyl)(2-nitrophenyl)amine (yield: 18%). 264 mg (0.939 mmol) of ((1-methylindole-3-yl)methyl)(2-nitrophenyl)amine were then dissolved in 10 ml of ethanol followed by the addition of 50 mg (0.047 mmol) of 10% Pd—C and stirring for 6 hours at room temperature in a hydrogen atmosphere. After completion of the reaction, the Pd—C was filtered out and the solvent was distilled off under reduced pressure to obtain 212 mg of ((1-methylindole-3-yl)methyl)(2-aminophenyl)amine (yield: 90%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe Pd—C was filtered out
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d761bcac4ab24090a0cc22654f31a6f8
Source dataset
uspto-grants-2007_02
Patent number
US07176320B2

Reaction notes

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