Tributylstannane → HCID 68693841, Verbindung

HRID 2238440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2238440
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:14])=[O:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:30]([CH2:38][CH:39]=[CH:40][Cl:41])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Cl:41][CH2:40][CH:39]1[C:2]2[C:11]3[CH:10]=[C:9]([S:12]([N:15]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)(=[O:13])=[O:14])[CH:8]=[CH:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:30]([C:31]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:37])[CH2:38]1

Komponenten

5

Edukt 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86620260HCID 86620260, Verbindung

Produkt 1

HCID 68693841HCID 68693841, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 213 (1.00 g, 1.53 mmol), Bu3SnH (550 mg, 1.83 mmol), and AIBN (50 mg, 0.31 mmol) in benzene (25 mL) was heated at reflux for 15 min, then concentrated under reduced pressure. The residue was partitioned between EtOAc and H2O and the EtOAc layer was washed with H2O, brine and dried and evaporated. The residue was purified by chromatography on silica gel, eluting with petroleum ether/EtOAc (9:1) to give tert-butyl 1-(chloromethyl)-8-[(dibenzylamino)sulfonyl]-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (214) (850 mg, 97%). A sample was recrystallised from Et2O/petroleum ether as colorless needles: mp 131-133° C.; 1H NMR (CDCl3) δ 8.30 (br s, 1H), 8.29 (d, J=1.5 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.66 (dd, J=8.6, 1.8 Hz, 1H), 7.23-7.15 (m, 6H), 7.09-7.03 (m, 4H), 4.41 (s, 4H), 4.28 (d, J=11.5 Hz, 1H), 4.15 (dd, J=11.6, 9.0 Hz, 1H), 4.02 (tt, J=9.0, 2.9 Hz, 1 H), 3.75 (dd, J=11.3, 3.5 Hz, 1H), 3.48 (dd, J=11.2, 9.3 Hz, 1H), 1.61 (s, 9H); 13C NMR δ 152.4, 142.7, 138.9, 135.5, 131.3, 130.5, 129.8, 128.9, 128.50, 128.46, 127.7, 124.3, 122.4, 120.3, 118.4, 81.8, 52.7, 50.5, 46.4, 41.4, 28.4. Anal. (C32H33ClN2O4S) C, H, N.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between EtOAc and H2O
  5. washthe EtOAc layer was washed with H2O, brine
  6. customdried
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with petroleum ether/EtOAc (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-90bfe7a4efeb4bf7bcbb032ff38cd4da
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718688B2

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