2-Methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine → 2-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine

HRID 536309

Reaction equation

HRID 536309 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([N:11]2[CH2:15][CH2:14][C@@H:13]([N:16]3[CH2:20][CH2:19][CH2:18][C@@H:17]3[CH3:21])[CH2:12]2)[N:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N:11]2[CH2:15][CH2:14][C@@H:13]([N:16]3[CH2:20][CH2:19][CH2:18][C@@H:17]3[CH3:21])[CH2:12]2)[N:3]=1

Participants

4

Reactant 1

HCID 674786772-Methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine

Product 1

HCID 674804612-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amineYield 32.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine (2.0 g, 6.89 mmol) and 10% Pd/C (200 mg) in ethanol (40 mL) was shaken on a parr shaker under 50 psi H2 for 18 h. The reaction mixture was filtered through a celite pad and concentrated to afford a dark red oil which was then purified by flash column chromatography (10% MeOH/CH2Cl2) to afford 580 mg (32% yield) of the title compound as an oil.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationconcentrated
  3. customto afford a dark red oil which
  4. customwas then purified by flash column chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-af3e9df8dc504b70ab1aff2832d8e575
Source dataset
uspto-grants-2014_10
Patent number
US08859588B2

Linked notes

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