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

HRID 1768089

Reaction equation

HRID 1768089 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8b7c7778a33449fcb86436e46f8aedca
Source dataset
uspto-grants-2007_06
Patent number
US07235578B2

Linked notes

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