Hydrochloric Acid → HCID 10737736, compound

HRID 1872042Notes

Reaction equation

HRID 1872042 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[C:12]1[NH2:18].Cl.[CH3:20][C:21](=O)[CH2:22][C:23](=O)[CH3:24]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:12]2[C:13](=[C:21]([CH3:20])[CH:22]=[C:23]([CH3:24])[N:18]=2)[C:14]([C:16]#[N:17])=[CH:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 10542510HCID 10542510, compound

Product 1

HCID 10737736HCID 10737736, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part C: A mixture of 18.51 g (0.0609 mole) of 1-(2-bromo-4-isopropylphenyl)-2-amino-4-cyano-pyrrole, 300 mL of ethanol, 0.6 mL of conc. hydrochloric acid, and 10 mL (9.75 g, 0.0974 mole) of 2,4-pentanedione was refluxed with stirring under a nitrogen atmosphere for 4 hrs. The mixture was allowed to cool and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed with 10% sodium bicarbonate solution, then with brine. The solution was dried with anhydrous sodium sulfate and evaporated to give 21.76 g of dark, tarry residue. The residue was chromatographed on silica gel by eluting in step gradients of 0, 10, 15, 20, 25, and 30% ethyl acetate in hexane. The initial fraction is 17.6 g (78%) 1-(2-bromo-4-isopropylphenyl)-3-cyano-4,6-dimethyl-7-azaindole; m.p. 105.8°. Mass spec: (m+H° =368.0749; calculated, 368.0762 (79Br). Rf =0.45 on silica gel thin layer chromatography with 70:30 hexane-ethyl acetate.

Workup

  1. temperaturewas refluxed
  2. temperatureto cool
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washThe solution was washed with 10% sodium bicarbonate solution
  6. dry with materialThe solution was dried with anhydrous sodium sulfate
  7. customevaporated
  8. customto give 21.76 g of dark, tarry residue
  9. customThe residue was chromatographed on silica gel
  10. washby eluting in step gradients of 0, 10, 15, 20, 25, and 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-dbbc1c884c374ba3a2f8d382eb0cd884
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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