N-(3-ethyl-1-((6-vinylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide → N-(3-ethyl-1-((6-ethylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79321Notes

Reaction equation

HRID 79321 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]=[CH2:32])[N:26]=2)[N:4]=1)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH3:32])[N:26]=2)[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67260793N-(3-ethyl-1-((6-vinylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67259621N-(3-ethyl-1-((6-ethylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 54.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N-(3-ethyl-1-((6-vinylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (11 mg, 0.026 mmol) in MeOH (3 mL) was added palladium on carbon (10% wt, 8 mg). The reaction mixture was purged with N2 three times followed by a purge with H2. A H2 balloon was applied to the reaction mixture. The mixture was stirred for one hour and filtered through a plug of silica gel. The plug was washed with MeOH (20 mL). The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (DCM/MeOH 10:1) to give the final product (6 mg). MS (ES+APCI) m/z=425 (M+H).

Workup

  1. customThe reaction mixture was purged with N2 three times
  2. customa purge with H2
  3. filtrationfiltered through a plug of silica gel
  4. washThe plug was washed with MeOH (20 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (DCM/MeOH 10:1)

Sources & evidence

ORD record
ord-d7d7a2dd0d4b45edb9d181f5ab7d339a
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…