Triphenylphosphine → 5-(2-Pyridin-4-ylfuran-3-yl)indan-1-one

HRID 1593440Notes

Reaction equation

HRID 1593440 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[C:26](=[O:30])[CH2:25][CH2:24]3)O1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C(O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:10]1[CH:11]=[CH:12][C:7]([C:3]2[O:4][CH:5]=[CH:6][C:2]=2[C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[C:26](=[O:30])[CH2:25][CH2:24]3)=[CH:8][CH:9]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 157218314-(3-Bromo-furan-2-yl)-pyridineHCID 185417105-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 694314975-(2-Pyridin-4-ylfuran-3-yl)indan-1-oneYield 62%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the product of Example 5 Step 5 (0.22 g, 1 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)indanone (0.25 g, 1 mmol) (WO98/45265) and potassium acetate (294 mg, 3 mmol) in dimethylformamide (2 ml), ethanol (2 ml) and water (2 ml) was treated with palladium (II) acetate (12 mg, 0.05 mmol) and triphenylphosphine (26.2 mg, 0.1 mmol) and heated under reflux for 5 hours. The reaction mixture was cooled to room temperature filtered through celite and concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (1:1) and methanol/ethyl acetate (1:9) to afford the title compound (0.17 g, 62%); MS(ES+) m/e 276 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. filtrationfiltered through celite and
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with hexane/ethyl acetate (1:1) and methanol/ethyl acetate (1:9)

Sources & evidence

ORD record
ord-13c957e11e474d0baf2da4a2f43d46db
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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