Tri(butyl)vinyltin → N-(2-Methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide

HRID 1162039Notes

Reaction equation

HRID 1162039 reaction equation
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])(=[O:13])=[O:12])[CH:3]=1.[CH2:22](C([Sn])=C(CCCC)CCCC)[CH2:23]CC>C(#N)C>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][S:11]([C:4]1[CH:3]=[C:2]([CH:22]=[CH2:23])[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 668932577-Iodo-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide2×

Product 1

HCID 66893854N-(2-Methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Iodo-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide (0.41 g, 1 mmol; Intermediate 58), tributylvinyltin (0.32 mL, 1.1 mmol), bis(triphenylphosphine)palladium diacetate (10 mg) and acetonitrile (3 mL) were heated under microwave irradiation to 180° C. for 5 min. The mixture was cooled, filtered and evaporated. The resulting oil was washed with hexane (2×50 mL), dissolved in diethyl ether (50 mL), filtered and evaporated to give the crude product which was crystallized from ethanol:water (3:1). Yield 0.19 g (61%) of an off white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.93 (s, 3H) 5.57 (dd, J=11.3, 1.0 Hz, 1H) 6.12 (dd, J=17.8, 1.0 Hz, 1H) 6.84-7.07 (m, 6H) 7.62 (d, J=1.8 Hz, 1H) 7.84 (d, J=1.8 Hz, 1H) 8.14 (d, J=2.3 Hz, 1H) 9.43 (s, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customevaporated
  4. washThe resulting oil was washed with hexane (2×50 mL)
  5. dissolutiondissolved in diethyl ether (50 mL)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-647012d2a0964c3a9d390402ba5787ec
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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