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

HRID 730433Notes

Reaction equation

HRID 730433 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:5]=[C:4]([C:22]#[N:23])[CH:3]=1.[C:24]([CH2:27][C:28](=O)[CH3:29])(=O)[CH3:25].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[F:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:6]2[C:2]3=[N:1][C:24]([CH3:25])=[CH:27][C:28]([CH3:29])=[C:3]3[C:4]([C:22]#[N:23])=[CH:5]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 516892Sodium BicarbonateHCID 230746485-Amino-1-[bis(4-fluorophenyl)methyl]-1H-pyrrole-3-carbonitrile

Product 1

HCID 690625951-[Bis(4-fluorophenyl)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-[bis(4-fluorophenyl)methyl]-1H-pyrrole-3-carbonitrile (13.9 g, 45.1 mmol) in ethanol (200 ml) was sequentially added acetylacetone (5.02 g, 50.2 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, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give the objective product as a solid material.

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

Sources & evidence

ORD record
ord-b681d3b3533d4b5ca9ac20453ac36437
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

Loading…