2-(Tributylstannyl)furan → HCID 178518634, compound

HRID 2257002Notes

Reaction equation

HRID 2257002 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10](I)=[C:9]([O:14]C)[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1.C([Sn](CCCC)(CCCC)[C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)CCC>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[C:9]([OH:14])[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1

Participants

6

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 18980002HCID 18980002, compound

Product 1

HCID 178518634HCID 178518634, compoundYield 55.2%

Reagents, catalysts & solvents 3

HCID 521585Tris(furan-2-yl)phosphaneCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of tri(2-furyl)phosphine (0.026 g) and tris(dibenzylideneacetone)dipalladium (O) (0.026 g) in toluene (50 mL) was allowed to stir for 10 minutes. To this solution was added 8-chloro-4-iodo-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz-[b]azepine (1.0 g), followed by 2-tributylstannylfuran (1.2 g). The reaction was heated to reflux for 0.5 hour, was allowed to cool, and the toluene was evaporated. The residue was triturated with hot hexanes (75 mL). The isolated solid was recrystallized from ethyl acetate/hexanes (1:1) to afford the title compound (0.44 g); mp 233°-234° C.; NMR: 11.47 (bs, 1), 7.79 (s, 1), 7.58 (d, 1, J=8.9), 7.34-7.31 (m, 2), 6.91 (d, 1, J=3.4), 6.61 (m, 1), 3.82 (s, 3). Analysis for C15H10ClNO4 0.5 H2O.: Calculated: C, 57.61; H, 3.54; N, 4.47; Found C, 57.77; H, 3.13; N, 4.46.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 0.5 hour
  3. temperatureto cool
  4. customthe toluene was evaporated
  5. customThe residue was triturated with hot hexanes (75 mL)
  6. customThe isolated solid was recrystallized from ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-60e33a0fd65649e8862932496323fc49
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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