(E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one → 1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)propan-1-one

HRID 2204548Notes

Reaction equation

HRID 2204548 reaction equation
[CH:1]1([C:7](=[O:29])/[CH:8]=[CH:9]/[C:10]2[N:11]=[C:12]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:13]3=[N:14][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([C:7](=[O:29])[CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=4)(=[O:21])=[O:20])[C:13]3=[N:14][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 58010004(E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one

Product 1

HCID 580100201-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)propan-1-oneYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one (0.050 g, 0.12 mmol) in EtOAc (5 mL) was added palladium (10% on carbon, 0.0065 g, 0.0061 mmol). The reaction mixture was purged with hydrogen and a hydrogen atmosphere was maintained via balloon. After about 1 h at ambient temperature, the reaction mixture was filtered and concentrated under reduced pressure to provide 1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)propan-1-one as an oil (0.050 g, 100%): LC/MS (Table 2, Method a) Rt=2.94 min; MS m/z: 412 (M+H)+.

Workup

  1. customThe reaction mixture was purged with hydrogen
  2. temperaturea hydrogen atmosphere was maintained via balloon
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b2d6c575ebc49ad9e1ccacf00a89559
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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