Hydrochloric Acid → 4-Aminomethyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole Dihydrochloride

HRID 1244985Notes

Reaction equation

HRID 1244985 reaction equation
[ClH:1].CO[N:4]=[CH:5][C:6]1[C:10]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:9]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[NH:8][CH:7]=1.C(OCC)C>[Pd].CO>[ClH:1].[ClH:1].[NH2:4][CH2:5][C:6]1[C:10]([C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)=[C:9]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[NH:8][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 1363804435-(4-Fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrole-3-carboxaldehyde O-methyloxime

Product 1

HCID 219227564-Aminomethyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole DihydrochlorideYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10 ml of 10% hydrochloric acid and 0.50 g of 10% palladium on carbon were added to a solution of 497 mg (1.68 mmol) of 5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrole-3-carboxaldehyde O-methyloxime [which was prepared as described in step 5(i) above] in 10 ml of methanol. The mixture was stirred under a hydrogen atmosphere at room temperature for 2 hours. At the end of this time, the reaction mixture was filtered and the filtrate thus obtained was concentrated by evaporation under reduced pressure. The residue was washed with diisopropylether and then with diethylether to give 391 mg (yield 68%) of the title compound as a yellowish orange powder.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customthe filtrate thus obtained
  3. concentrationwas concentrated by evaporation under reduced pressure
  4. washThe residue was washed with diisopropylether

Sources & evidence

ORD record
ord-1d2786f03a764c9b814277402c53c70a
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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