Triphenylphosphine → 5-(1-Methoxyimino-indan-5-yl)-4-pyridin-4-yl-furan-2-carbaldehyde

HRID 271515Notes

Reaction equation

HRID 271515 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[O:20])[O:5][C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[N:16][O:17][CH3:18])[CH2:11][CH2:10]2.C([Sn](CCCC)(CCCC)[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)CCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][N:16]=[C:12]1[C:13]2[C:9](=[CH:8][C:7]([C:6]3[O:5][C:4]([CH:19]=[O:20])=[CH:3][C:2]=3[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[CH:15][CH:14]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 867607594-Bromo-5-(1-methoxyimino-indan-5-yl)-furan-2-carbaldehyde

Product 1

HCID 867607605-(1-Methoxyimino-indan-5-yl)-4-pyridin-4-yl-furan-2-carbaldehydeYield 69%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A degassed mixture of the product of Step 4 (2.0 g, 6.0 mmol) and 4-tributylstannylpyridine (2.5 g, 6.8 mmol) in toluene (100 ml) was treated with triphenylphosphine (156 mg, 0.6 mmol) and palladium acetate (67 mg, 0.3 mmol) then heated under reflux for 60 hours. The reaction mixture was concentrated in vacuo and the product purified by silica gel chromatography eluting with ethyl acetate/hexane (1:1) and then ethyl acetate to give the title compound (1.37 g, 69%); MS(ES+) m/e 333 [M+H]+.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 60 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe product purified by silica gel chromatography
  5. washeluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-d59478a4e454451788f17817b8af18ac
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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