Hydrochloric Acid → 1-[(4-Fluorophenyl)(phenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 730425Notes

Reaction equation

HRID 730425 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:4]([C:21]#[N:22])[CH:3]=1.[C:23]([CH2:26][C:27](=O)[CH3:28])(=O)[CH3:24].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:6]2[C:2]3=[N:1][C:23]([CH3:24])=[CH:26][C:27]([CH3:28])=[C:3]3[C:4]([C:21]#[N:22])=[CH:5]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 516892Sodium BicarbonateHCID 690583295-Amino-1-((4-fluorophenyl)(phenyl)methyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 690584651-[(4-Fluorophenyl)(phenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-amino-1-[(4-fluorophenyl)(phenyl)methyl]-1H-pyrrole-3-carbonitrile (13.7 g, 47.0 mmol) in ethanol (200 ml) was sequentially added acetylacetone (5.66 g, 56.6 mmol) and concentrated hydrochloric acid (2.0 ml). The mixture was heated under reflux for 3 hours, poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate and hexane.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-68d0f948f7934c7889bcc307f33ee8f4
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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