Sodium Carbonate → HCID 86213593, compound

HRID 1593441Notes

Reaction equation

HRID 1593441 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:9])[CH3:8].[CH3:10][O:11][N:12]=[C:13]1[C:21]2[C:16](=[CH:17][C:18](B(O)O)=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][O:11][N:12]=[C:13]1[C:21]2[C:16](=[CH:17][C:18]([C:2]3[CH:6]=[CH:5][O:4][C:3]=3[C:7](=[O:9])[CH3:8])=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 113214142-Acetyl-3-bromofuranHCID 734146811-Methoxyimino-indan-5-boronic acid

Product 1

HCID 86213593HCID 86213593, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1-(3-bromofuran-2-yl)ethanone (A. Tanaka et al., J. Heterocycl. Chem., 1995, 32, 4 1289) (2.5 g, 13.2 mmol), the product of Example 5 Step 6 (2.83 g, 13.9 mmol), sodium carbonate (2.8 g, 27.7 mmol) in toluene (40 ml) and water (14 ml) was treated with triphenylphosphine (0.35 g, 1.3 mmol) and palladium acetate (150 mg, 0.66 mmol) and heated under reflux for 18 hours. After cooling to room temperature, the mixture was filtered through celite and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and saturated brine, dried (MgSO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with a mixture of diethyl ether/dichloromethane (5:95) to afford the title compound (2.5 g, 70%); MS(ES+) m/e 270 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. filtrationthe mixture was filtered through celite
  4. additionthe filtrate diluted with water and ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with water and saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customthe residue chromatographed on silica gel eluting with a mixture of diethyl ether/dichloromethane (5:95)

Sources & evidence

ORD record
ord-3944719d1f374b58b2f72daa1657701e
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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