6-(6-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3-vinyl-quinoline → 3-Ethyl-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline

HRID 655305Notes

Reaction equation

HRID 655305 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([CH:22]=[CH2:23])=[CH:15]4)=[N:9][N:10]=2)[N:7]=1>[Pd].C(O)C>[CH2:22]([C:16]1[CH:17]=[N:18][C:19]2[C:14]([CH:15]=1)=[CH:13][C:12]([CH2:11][C:8]1[N:6]3[N:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]3=[N:10][N:9]=1)=[CH:21][CH:20]=2)[CH3:23]

Participants

4

Reactant 1

HCID 249669426-(6-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3-vinyl-quinoline

Product 1

HCID 593203623-Ethyl-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinolineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3-vinyl-quinoline (20 mg, 0.0664 mmol) and palladium on carbon (10% wt, 20 mg) in ethanol (1.5 mL) under a hydrogen atmosphere was stirred vigorously at ambient temperature for 4 hours. The mixture was then filtered through a pad of celite and the filtrate concentrated to provide the title compound (15 mg, 75% yield). Analytical data presented in Table 1.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-42d2c129b2264e869cef1b9d57b7c363
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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