6-Chloro-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridine → 6-Chloro-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1054966Notes

Reaction equation

HRID 1054966 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([CH:11]=[CH:12][C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:14]=3)[N:10]=2)[CH:7]=1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:14]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 1235482036-Chloro-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 900266306-Chloro-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-[1,2,4]triazolo[1,5-a]pyridineYield 15.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 6-chloro-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridine (50 mg, 152 μmol, Eq: 1.00) and 5% Pd on Ba2SO4 (150 mg) in EtOAc (5 ml) was stirred under hydrogen (1 atm) for 2 h. The mixture was filtered over Celite and the residue purified by prep. HPLC to give the desired product (7.7 mg, 15%) as a white solid. MS: m/z=331.9 (M+H+)

Workup

  1. filtrationThe mixture was filtered over Celite
  2. customthe residue purified by prep

Sources & evidence

ORD record
ord-a06b3ca0ee48487cad62832b3760660c
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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