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

HRID 1768089

反応式

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

参加物

実験手順

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).

後処理

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

出典と根拠

ORDレコード: ord-8b7c7778a33449fcb86436e46f8aedca
出典データセット: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07235578B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 2

実験手順

後処理

出典と根拠

関連ノート