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

HRID 342804

반응식

HRID 342804 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-04938e7e5b234ba98711ff0e387cc7b4
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859044

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