Diphenyl sulfide → Ethyl 3-(4-methoxybutyl)imidazo[1,2-a]pyridine-2-carboxylate

HRID 2169012Notes

Reaction equation

HRID 2169012 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]/[CH:5]=[CH:6]/[C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C1(SC2C=CC=CC=2)C=CC=CC=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 8766Diphenyl sulfideHCID 58355141ethyl 3-[(1E)-4-methoxybut-1-en-1-yl]imidazo[1,2-a]pyridine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58355561Ethyl 3-(4-methoxybutyl)imidazo[1,2-a]pyridine-2-carboxylateYield 48.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-[(1E)-4-methoxybut-1-en-1-yl]imidazo[1,2-a]pyridine-2-carboxylate (530 mg) and diphenyl sulfide (3.6 mg) were dissolved in ethyl acetate (13 ml), 10% palladium carbon (50% in water) (53 mg) was added and the mixture was stirred in a hydrogen stream at ambient temperature and normal pressure for 2.5 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (260 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washa fraction eluted with ethyl acetate
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-00fdd5f4a2c449f5ad2b339a53cc4483
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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