3-(2-Phenyl-pyridin-4-yl)-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-imidazo[1,2-a]pyridine → 3-(2-Phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine

HRID 383280Notes

Reaction equation

HRID 383280 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([C:22]5[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=5)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]5[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]5)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 252609473-(2-Phenyl-pyridin-4-yl)-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-imidazo[1,2-a]pyridine

Product 1

HCID 252609443-(2-Phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(2-Phenyl-pyridin-4-yl)-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-imidazo[1,2-a]pyridine (Ex. 1.190) (1.0 eq, 1.15 mmol, 0.51 g) in dissolved in MeOH (20 ml) and Pd/C (10%, 1.15 eq, 1.32 mmol, 140 mg) and the reaction mixture is hydrogenated at rt for 16 h (4 bar pressure). The solid is removed by filtration and the solvent is evaporated to dryness to yield 3-(2-phenyl-pyridin-4-yl)-7-piperidin-4-yl-imidazo[1,2-a]pyridine as a light yellow solid which did not require any further purification; [M+H]+=391

Workup

  1. customThe solid is removed by filtration
  2. customthe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-5f03196cbdda444894b45e46785d0af9
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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