3-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione → HCID 86750789, compound

HRID 1779450Notes

Reaction equation

HRID 1779450 reaction equation
[CH2:1](/[C:8](=[CH:13]\[C:14]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=2)[C:17]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:16][C:15]=1[Cl:31])/[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:32]([O:35][C:36]1[C:37](=[O:54])[C:38](=[O:53])[C:39]=1[Sn](CCCC)(CCCC)CCCC)([CH3:34])[CH3:33]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[CH2:1](/[C:8](=[CH:13]\[C:14]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:39]3[C:38](=[O:53])[C:37](=[O:54])[C:36]=3[O:35][CH:32]([CH3:34])[CH3:33])=[CH:22][CH:21]=2)[C:17]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:16][C:15]=1[Cl:31])/[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 27366833-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dioneHCID 67707702HCID 67707702, compound

Product 1

HCID 86750789HCID 86750789, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of Example 30 (c) (0.8 g), 3-isopropoxy-4-tributylstannylcyclobut-3-ene-1,2-dione (0.9 g), tetrakis(triphenylphosphine)palladium(0) (0.2 g), cuprous iodide (0.1 g) and dry dimethylformamide (5 ml) was stirred at ambient temperature under a nitrogen atmosphere for approximately 17 hours. The solvent was evaporated under reduced pressure and the resulting residue was dissolved in diethyl ether (150 ml). The solution obtained was washed with saturated aqueous ammonium chloride solution (50 ml), then with saturated aqueous potassium fluoride solution (2×50 ml) and then dried over magnesium sulphate. The solvent was evaporated and the residue obtained was purified by flash chromatography on silica gel (eluting with dichloromethane/methanol (50:1)) to give the intermediate compound (E)-methyl 2-benzyl-3-[2-butyl-4-chloro-1-[4-(2-isopropoxy-3,4-dioxocyclobut-1-en-1-yl)benzyl]-1H-imidazol-5-yl]propenoate as an oil (0.4 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in diethyl ether (150 ml)
  3. customThe solution obtained
  4. washwas washed with saturated aqueous ammonium chloride solution (50 ml)
  5. dry with materialwith saturated aqueous potassium fluoride solution (2×50 ml) and then dried over magnesium sulphate
  6. customThe solvent was evaporated
  7. customthe residue obtained
  8. customwas purified by flash chromatography on silica gel (eluting with dichloromethane/methanol (50:1))

Sources & evidence

ORD record
ord-146bf441f1ed49b0b589a6c719bff2c2
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

Loading…