Ethanol → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 388122Notes

Reaction equation

HRID 388122 reaction equation
[C:1]1([CH:7]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][CH:21]=[N:22]4)[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](C1C(NC(C2C=CC=CC=2)C)=NC(C2C=CC=C3C=2C=CC=N3)=CC=1)([O-])=O.[CH2:55]([OH:57])C>[Pd]>[C:1]1([CH:7]([N:9]2[C:10]3=[N:11][C:12]([C:17]4[CH:26]=[CH:25][CH:24]=[C:23]5[C:18]=4[CH:19]=[CH:20][CH:21]=[N:22]5)=[CH:13][CH:14]=[C:15]3[NH:16][C:55]2=[O:57])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 666998813-Nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amineHCID 77571172N2-(1-Phenylethyl)-6-(quinolin-5-yl)pyridine-2,3-diamine

Product 1

HCID 249846803-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N2-(1-Phenylethyl)-6-(quinolin-5-yl)pyridine-2,3-diamine. A solution of 3-nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amine (2.36 g, 6.37 mmol) in ethanol (175 mL) was purged with nitrogen for several min. Following addition of palladium on carbon (245 mg, 2.29 mmol), the flask was evacuated and a hydrogen filled balloon was placed on the reaction. After stirring at room temperature for 18 h, the reaction was filtered and the solvent removed under reduced pressure to afford the title compound (1.89 g, 87% yield). MS (ESI) m/z 341.3 [M+1]+.

Workup

  1. customthe flask was evacuated
  2. customa hydrogen filled balloon was placed on the reaction
  3. filtrationthe reaction was filtered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-de9b307c07764f3db4b6122aca1685c2
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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