Triphenylphosphine → 5-(5-Hydroxymethyl-2-pyridin-4-yl-furan-3-yl)indan-1-one

HRID 271537Notes

Reaction equation

HRID 271537 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:13][OH:14])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.CC1(C)C(C)(C)OB([C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[C:28](=[O:32])[CH2:27][CH2:26]3)O1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O.O.C(O)C>[OH:14][CH2:13][C:4]1[O:5][C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:2]([C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[C:28](=[O:32])[CH2:27][CH2:26]3)[CH:3]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 185417105-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-oneHCID 69314671(4-Bromo-5-pyridin-4-yl-furan-2-yl)-methanol

Product 1

HCID 693172355-(5-Hydroxymethyl-2-pyridin-4-yl-furan-3-yl)indan-1-oneYield 125.4%

Reagents, catalysts & solvents 4

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

Procedure

The product from Step 2 (737 mg, 2.9 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)indanone (0.25 g, 1 mmol) (WO98/45265) (750 mg, 2.9 mmol), potassium acetate (854 mg, 8.7 mmol), triphenylphosphine (79 mg, 0.3 mmol) and palladium (II) acetate (34 mg, 0.15 mmol) were heated at 95° C. in 1:1:1 ethanol:water:N,N-dimethylformamide (10 ml) for 16 hours. After cooling the solution was partitioned between ethylacetate/water and the aqueous phase extracted with ethylacetate (×3). The combined organic extracts were washed with water (×3), brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with ethylacetate to afford the title product (383 mg, 43%); MS(ES+) m/e 306 [M+H]+.

Workup

  1. temperatureAfter cooling the solution
  2. customwas partitioned between ethylacetate/water
  3. extractionthe aqueous phase extracted with ethylacetate (×3)
  4. washThe combined organic extracts were washed with water (×3), brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with ethylacetate

Sources & evidence

ORD record
ord-bfe12765e6c4489d9a96fced60e7ea21
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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