Hydrochloric Acid → HCID 10737736, compound

HRID 1251487Notes

Reaction equation

HRID 1251487 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

Sources & evidence

ORD record
ord-e642ebcc940d48aabf73ceab92a3db77
Source dataset
uspto-grants-2002_01
Patent number
US06342503B1

Reaction notes

Loading…