Benzenesulfinic acid → 5-amino-1-(chloromethyl)-3-((5,6,7-trimethoxyindol-2-yl)carbonyl)-1,2-dihydro-3H-benz(e)indole

HRID 1768089

Reaktionsgleichung

Reaktionsgleichung von HRID 1768089
C1(S(O)=O)C=CC=CC=1.[Na].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C([NH:29][C:30]1[C:31]2[CH:61]=[CH:60][CH:59]=[CH:58][C:32]=2[C:33]2[CH:34]([CH2:56][Cl:57])[CH2:35][N:36]([C:39]([C:41]3[NH:42][C:43]4[C:48]([CH:49]=3)=[CH:47][C:46]([O:50][CH3:51])=[C:45]([O:52][CH3:53])[C:44]=4[O:54][CH3:55])=[O:40])[C:37]=2[CH:38]=1)C=C>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:57][CH2:56][CH:34]1[C:33]2[C:32]3[CH:58]=[CH:59][CH:60]=[CH:61][C:31]=3[C:30]([NH2:29])=[CH:38][C:37]=2[N:36]([C:39]([C:41]2[NH:42][C:43]3[C:48]([CH:49]=2)=[CH:47][C:46]([O:50][CH3:51])=[C:45]([O:52][CH3:53])[C:44]=3[O:54][CH3:55])=[O:40])[CH2:35]1

Komponenten

7

Edukt 4

HCID 12057Benzenesulfinic acidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 5360545SodiumHCID 9806196N-allyl-1-(chloromethyl)-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2-dihydro-3H-benzo[e]indol-5-amine

Produkt 1

HCID 3917005-amino-1-(chloromethyl)-3-((5,6,7-trimethoxyindol-2-yl)carbonyl)-1,2-dihydro-3H-benz(e)indoleAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzenesulfinic acid, sodium salt (25 mg, 0.15 mmol) and camphorsulfonic acid (40 mg, 0.17 mmol) were added to a solution of 10a (30 mg, 0.059 mmol) in dichloromethane (5 mL). Pd(Ph3P)4 (5 mg, 0.004 mmol) was added and the reaction mixture was stirred at an ambient temperature for 30 min. The mixture was purified directly via a silica gel column. Elution with EtOAc/petroleum ether (1:1) gave 1-(chloromethyl)-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2-dihydro-3H-benzo[e]indol-5-amine (11a) (22 mg, 80%), spectroscopically identical to an authentic sample (Atwell et al., J. Org Chem., 1998, 63, 9414).

Aufarbeitung

  1. customThe mixture was purified directly via a silica gel column
  2. washElution with EtOAc/petroleum ether (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8b7c7778a33449fcb86436e46f8aedca
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235578B2

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