HCID 11149071, compound → HCID 67273641, compound

HRID 1696749Notes

Reaction equation

HRID 1696749 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[C:11]1[N:16]=[C:15]([NH2:17])[CH:14]=[C:13]([CH3:18])[CH:12]=1>CO.[Pd]>[CH3:18][C:13]1[CH:12]=[C:11]([CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[N:16]=[C:15]([NH2:17])[CH:14]=1

Participants

4

Reactant 1

HCID 11149071HCID 11149071, compound

Product 1

HCID 67273641HCID 67273641, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-(3,4-Dihydro-naphthalen-2-yl)-4-methyl-pyridin-2-ylamine (CAS 521917-11-3) (1.8 g) is dissolved in methanol (30 mL) under an Ar atmosphere. To the obtained solution Pd/C (10%; 250 mg) was added. After that hydrogen was flushed through the reaction mixture (1 bar) for 2 h at 25° C. After that the catalyst was removed by filtration, the filtrate was evaporated to dryness and the crude product was purified by flash chromatography (200 g SiO2, CH2Cl2/1% MeOH) to yield 4-methyl-6-(1,2,3,4-tetrahydro-naphthalen-2-yl)-pyridin-2-ylamine (970 mg) as an oil.

Workup

  1. customAfter that hydrogen was flushed through the reaction mixture (1 bar) for 2 h at 25° C
  2. customAfter that the catalyst was removed by filtration
  3. customthe filtrate was evaporated to dryness
  4. customthe crude product was purified by flash chromatography (200 g SiO2, CH2Cl2/1% MeOH)

Sources & evidence

ORD record
ord-0c53a41e37bc4987a0644ef896a59883
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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