HCID 69589195, compound → HCID 21922786, compound

HRID 1244981Notes

Reaction equation

HRID 1244981 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([CH:19]=[CH:20][C:21]#[N:22])[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1>O1CCCC1.CO.[Pd]>[C:21]([CH2:20][CH2:19][C:11]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[NH:9][CH:10]=1)#[N:22]

Participants

5

Reactant 1

HCID 69589195HCID 69589195, compound

Product 1

HCID 21922786HCID 21922786, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.94 g (10.16 mmol) of 3-[2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrol-4-yl]acrylonitrile [prepared as described in step (iv) above] were dissolved in a mixture of 20 ml of tetrahydrofuran and 20 ml of methanol, after which 2.94 g of 10% palladium on carbon were added to the solution. The mixture was stirred under a hydrogen atmosphere at room temperature for 8 hours. At the end of this time, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was washed with a mixture of 30 ml of diethyl ether and 30 ml of ethanol to give 1.80 g (yield 61%) of the title compound as a pale orange powder.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe resulting residue was washed with a mixture of 30 ml of diethyl ether and 30 ml of ethanol

Sources & evidence

ORD record
ord-4b85b458a2b84d6e98180eb16ae366f4
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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