6-Nitro-1-pyrimidin-5-ylmethyl-1H-indole → 1-Pyrimidin-5-ylmethyl-1H-indol-6-ylamine

HRID 1713410Notes

Reaction equation

HRID 1713410 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[N:18][CH:19]=2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.C(O)(C)C.[Pd]>[N:16]1[CH:15]=[C:14]([CH2:13][N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=3)[CH:8]=[CH:9]2)[CH:19]=[N:18][CH:17]=1

Participants

5

Reactant 1

HCID 667755866-Nitro-1-pyrimidin-5-ylmethyl-1H-indole

Product 1

HCID 667756801-Pyrimidin-5-ylmethyl-1H-indol-6-ylamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Nitro-1-pyrimidin-5-ylmethyl-1H-indole (4.1 g, 16.1 mmol) was dissolved in 100 mL of THF and 100 mL of isopropanol. Pd/C (2 g) was added and the mixture was stirred under an H2-atmosphere (balloon) for 2 hours. The mixture was filtered over Celite and washed with ethyl acetate affording the title compound after concentration (3.5 g, 15.6 mmol, 97%).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. washwashed with ethyl acetate affording the title compound
  3. concentrationafter concentration (3.5 g, 15.6 mmol, 97%)

Sources & evidence

ORD record
ord-9daf5a0422db46d292aa17e10bc2a7d7
Source dataset
uspto-grants-2010_09
Patent number
US07795280B2

Reaction notes

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