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

HRID 2256998Notes

Reaction equation

HRID 2256998 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[S:40][CH:41]=[CH:42][CH:43]=1)CCC>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27](=[O:28])[C:26]([C:39]3[S:40][CH:41]=[CH:42][CH:43]=3)=[C:25]([O:30][CH3:31])[C:24](=[O:32])[NH:23][C:22]=2[CH:33]=1

Participants

5

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 18980002HCID 18980002, compound

Product 1

HCID 189800434-(2-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tri(2-furyl)phosphine (0.036 g) and tris(dibenzylideneacetonedipalladium (O) (0.26 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-tributylstannylthiophene (1.24 g). The reaction was heated to reflux for 1.5 hours, was allowed to cool, and the toluene was evaporated. The residue was triturated with hot hexanes (75 mL). The title compound was afforded upon filtration (0.76 g); mp >240; NMR: 11.47 (bs, 1), 7.73 (dd, 1, J=5.1, 0.8), 7.60 (d, 1, J=7.9), 7.51 (dd, 1, J=4.0), 7.33 (d, 1, J=7.8), 7.31 (s, 1), 7.14 (dd, 1, J=5.1, 4.1), 3.88 (s, 3). Analysis for C15H10O3SClN: Calculated: C, 56.34; H, 3.15; N, 4.38; Found C, 55.96; H, 3.34; N, 4.33.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. customthe toluene was evaporated
  5. customThe residue was triturated with hot hexanes (75 mL)

Sources & evidence

ORD record
ord-f63273753c15400eb2115d3bb1e4b59e
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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