HCID 21922669, compound → HCID 9797188, compound

HRID 1244993Notes

Reaction equation

HRID 1244993 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][CH:12]=[C:13]([C:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=3)[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1>[Pd].CO>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][CH:12]=[C:13]([CH:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21922669HCID 21922669, compound

Product 1

HCID 9797188HCID 9797188, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

120 mg of 10% palladium on carbon were added to a solution of 120 mg (0.306 mmol) of 2-(4-fluorophenyl)-3-(pyridin-4-yl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrole dihydrochloride [prepared as described in Example 10 above] in 10 ml of methanol. The resulting mixture was stirred under a hydrogen atmosphere at room temperature for 1 hour, after which the reaction mixture was filtered. The filtrate thus obtained was concentrated by evaporation under reduced pressure. Water was added to the resulting residue and then this mixture was made alkaline with a 1 N aqueous solution of sodium hydroxide. The resulting precipitate was collected by filtration to give 84 mg (yield 85%) of the title compound as a pale red powder.

Workup

  1. filtrationafter which the reaction mixture was filtered
  2. customThe filtrate thus obtained
  3. concentrationwas concentrated by evaporation under reduced pressure
  4. additionWater was added to the resulting residue
  5. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e25c228b8c8747b58edd2550df9f92af
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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