1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-3-(1-methyl-1H-imidazol-2-yl)furo[2,3-b]pyridin-2-yl]-2,2-dimethylpropan-1-one

HRID 8824Notes

Reaction equation

HRID 8824 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([O:14][CH2:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:22]([C:24]2[N:25]([CH3:29])[CH:26]=[CH:27][N:28]=2)=O)=[CH:10][C:9]=1[C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1.N12CCCN=C1CCCCC2>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([C:16](=[O:21])[C:17]([CH3:18])([CH3:19])[CH3:20])=[C:22]([C:24]3[N:25]([CH3:29])[CH:26]=[CH:27][N:28]=3)[C:11]2=[CH:10][C:9]=1[C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219848141-({6-(2-Chlorophenyl)-5-(4-chlorophenyl)-3-[(1-methyl-1H-imidazol-2-yl)carbonyl]pyridin-2-yl}oxy)-3,3-dimethylbutan-2-one

Product 1

HCID 219849271-[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-3-(1-methyl-1H-imidazol-2-yl)furo[2,3-b]pyridin-2-yl]-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.094 g (0.18 mmol) of the product of Step B and 0.027 g (0.18 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 2 mL DMF was placed in a 10 mL reaction tube of a CEM Corporation Discover 300 Watt microwave reactor. The reaction vessel was sealed, placed in the microwave reactor and heated at 150° C. for 5 min. After the reaction vessel had cooled again to room temperature, the reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was separated, washed with aq. NaHCO3, brine, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–75% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 504.2 (M+1), 506.0 (M+3); Rt=3.39 min.

Workup

  1. customwas placed in a 10 mL reaction tube of a CEM Corporation Discover 300 Watt microwave reactor
  2. customThe reaction vessel was sealed
  3. temperatureAfter the reaction vessel had cooled again to room temperature
  4. customthe reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3 solution
  5. customThe organic layer was separated
  6. washwashed with aq. NaHCO3, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 0–75% EtOAc-hexane
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-ba1760b26e374dbd82c6ff5fe2302808
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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