Sodium Carbonate → HCID 9944717, compound

HRID 1245004Notes

Reaction equation

HRID 1245004 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.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1.CO.[Pd]>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:11][CH:12]=[C:13]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 21922669HCID 21922669, compound

Product 1

HCID 9944717HCID 9944717, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 7237O-XyleneSolvent

Procedure

450 mg (1.15 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] were suspended in a mixture of 25 ml of xylene and 2 ml of methanol and 450 mg of 10% palladium on carbon and 320 mg (2.30 mmol) of sodium carbonate were added to the suspension. The resulting mixture was heated under reflux for 4 hours. At the end of this time, the reaction mixture was filtered and the resulting filtrate was concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 10:1:1 by volume mixture of ethyl acetate, methanol and isopropylamine as the eluant to give 192 mg (yield 53%) of the title compound as a pale yellow powder.

Workup

  1. additionwere added to the suspension
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 4 hours
  4. filtrationAt the end of this time, the reaction mixture was filtered
  5. concentrationthe resulting filtrate was concentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by chromatography on a silica gel column
  8. additionby volume mixture of ethyl acetate, methanol and isopropylamine as the eluant

Sources & evidence

ORD record
ord-21734abbcd894c7ab5caee9e016630cb
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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