2,5-Bis(tri-n-butylstannyl)furan → HCID 178502855, compound

HRID 853808Notes

Reaction equation

HRID 853808 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([NH:8][O:9][CH3:10])=[NH:7])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[O:19][C:20]([Sn](CCCC)(CCCC)CCCC)=[CH:21][CH:22]=1)CCC>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][O:9][NH:8][C:6]([C:5]1[CH:11]=[CH:12][C:2]([C:20]2[O:19][C:18]([C:2]3[CH:12]=[CH:11][C:5]([C:6](=[NH:7])[NH:8][O:9][CH3:10])=[CH:4][N:3]=3)=[CH:22][CH:21]=2)=[N:3][CH:4]=1)=[NH:7]

Participants

5

Reactant 2

HCID 115782772,5-Bis(tri-n-butylstannyl)furanHCID 178502858HCID 178502858, compound

Product 1

HCID 178502855HCID 178502855, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Continuing with Scheme 5, a mixture of 26 (6, mmol), 2,5-bis(tri-n-butylstannyl)furan (3 mmol) and tetrakis(triphenylphosphine)-palladium(0) (150 mg) in dry 1,4-dioxane (20 mL) was heated under nitrogen at reflux (100–110° C.) for 24 h. The solvent was evaporated under reduced pressure, dissolved in methylene chloride, and the solution was passed through celite to remove Pd. The solution was evaporated, the solid was filtered and washed with hexanes to afford 27 (SiO2, hexanes/EtOAc, 1:1), yield 35%, mp 228–230° C. 1H nmr (DMSO-d6); δ 3.80 (s, 6H), 6.31 (s, 4H), 7.34 (s, 2H), 7.98 (d, J=8.4 Hz, 2H), 8.13 (dd, J=8.4, 2.4 Hz, 2H). 8.88 (d, J=2.4 Hz, 2H). 13C nmr; δ 153.5, 148.9, 148.3, 147.0, 134.1, 126.8, 118.1, 112.0, 60.7. MS (m/z, rel.int.); 366 (M+, 100), 335 (25), 319 (30), 288 (40). High resolution mass calcd. for C18H18N6O3: 366.14404. Observed: 366.14012.

Workup

  1. temperaturewas heated under nitrogen
  2. temperatureat reflux (100–110° C.) for 24 h
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutiondissolved in methylene chloride
  5. customto remove Pd
  6. customThe solution was evaporated
  7. filtrationthe solid was filtered
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-ad19f6718fb247be8be3b134a543e6be
Source dataset
uspto-grants-2007_08
Patent number
US07256203B2

Reaction notes

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