Isopropenyl acetate → 1-(4-Nitro-benzyl)-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester

HRID 342804

反応式

HRID 342804 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:44][C:45]([CH3:47])=[CH2:46])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:46][C:45](=[O:44])[CH3:47])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 7916Isopropenyl acetateHCID 80271Tri-o-tolylphosphineHCID 11964040Methoxytri-n-butylstannaneHCID 543953975-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl ester

生成物 1

HCID 544815121-(4-Nitro-benzyl)-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester収率 61.8%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

A solution of 5-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl ester (3.28 g, 8.13 mmol), tributyltin methoxide (3.92 g, 3.51 ml, 12.2 mmol), isopropenyl acetate (1.22 g, 1.34 ml, 12.2 mmol), palladium (II) acetate (91 mg, 0.41 mmol) and tri-o-tolylphosphine (248 mg, 0.813 mmol) in toluene (10 ml) was heated at about 95° C. under nitrogen for about 3 hours. The reaction solution was cooled, concentrated in vacuo, and subjected to flash chromatography on silica (200 g, gradient from 10% ethyl acetate/hexane to 40% ethyl acetate/hexane), and then the partially pure product was recrystallized from toluene/heptane to give the title compound (1.91 g).

後処理

  1. temperatureThe reaction solution was cooled
  2. concentrationconcentrated in vacuo
  3. customthe partially pure product was recrystallized from toluene/heptane

出典と根拠

ORDレコード
ord-04938e7e5b234ba98711ff0e387cc7b4
出典データセット
uspto-grants-1999_01
特許番号
US05859044

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