Tris(furan-2-yl)phosphane → 4-(3-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

HRID 2392560Notes

Reaction equation

HRID 2392560 reaction equation
O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27](=[O:28])[C:26](I)=[C:25]([O:30][CH3:31])[C:24](=[O:32])[NH:23][C:22]=2[CH:33]=1.C([Sn](CCCC)(CCCC)[C:39]1[CH:43]=[CH:42][S:41][CH:40]=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]>[S:41]1[CH:42]=[CH:43][C:39]([C:26]2[C:27](=[O:28])[C:21]3[CH:20]=[CH:19][C:18]([Cl:17])=[CH:33][C:22]=3[NH:23][C:24](=[O:32])[C:25]=2[O:30][CH3:31])=[CH:40]1

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 10959689Stannane, tributyl-3-thienyl-HCID 18980002HCID 18980002, compound

Product 1

HCID 189800404-(3-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepineYield 33.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of tri(2-furyl)phosphine (0.046 g) and tris(dibenzylideneacetone)dipalladium (O) (0.046 g) in toluene (75 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 (1.82 g), followed by 3-tributylstannylthiophene (2.2 g). The reaction was heated to reflux for 3 hours. After allowing the reaction mixture to cool to room temperature and stir for 16 hours, a solid precipitated. The filtered solid was recrystallized from ethyl acetate/methanol (2:1) to afford the title compound (0.54 g); NMR: 11.49 (bs, 1), 7.78 (m, 1), 7.63 (d, 1, J=8.4), 7.52 (m, 1), 7.38 (d, 1, J=1.9), 7.30 (dd, 1, J=8.6, 2.1), 7.20 (m, 1), 3.75 (s, 3).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. stirringstir for 16 hours
  4. customa solid precipitated
  5. customThe filtered solid was recrystallized from ethyl acetate/methanol (2:1)

Sources & evidence

ORD record
ord-b5c477219daf4ec0b1c7f9b7488b8c85
Source dataset
uspto-grants-1998_09
Patent number
US05801168

Reaction notes

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