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

HRID 8811

Reaction equation

HRID 8811 reaction equation
[C:1]([C:4]1[C:5]([O:24][CH2:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[N:6][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:9]=1)(=O)[CH3:2].N12CCCN=C1CCCCC2>CN(C=O)C>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:7]1[N:6]=[C:5]2[O:24][C:25]([C:26](=[O:31])[C:27]([CH3:29])([CH3:30])[CH3:28])=[C:1]([CH3:2])[C:4]2=[CH:9][C:8]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219848171-{[3-Acetyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridin-2-yl]oxy}-3,3-dimethylbutan-2-one

Product 1

HCID 102525661-[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-3-methylfuro[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 0.432 g (0.95 mmol) of the product of Step B, 250 A (1.67 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 10 min. After the reaction mixture had cooled to room temperature, it was partitioned between EtOAc and 10% aq. NaHSO4 and extracted. The organic layer was washed with 10% aq. NaHSO4, water, brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–10% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 438.1 (M+1), 440.1 (M+3); Rt=4.72 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 mixture had cooled to room temperature
  4. customit was partitioned between EtOAc and 10% aq. NaHSO4
  5. extractionextracted
  6. washThe organic layer was washed with 10% aq. NaHSO4, water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 0–10% EtOAc-hexane
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-3c143f1741694798b05a671e25e7f738
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Linked notes

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