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

HRID 342800

반응식

HRID 342800 반응식
[CH2:1]([O:8][C:9]([C:11]1[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:49][C:50]([CH3:52])=[CH2:51])(=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:8][C:9]([C:11]1[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([CH2:51][C:50](=[O:49])[CH3:52])=[CH:15][CH:14]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 7916Isopropenyl acetateHCID 80271Tri-o-tolylphosphineHCID 11964040Methoxytri-n-butylstannaneHCID 538099935-Bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic Acid Benzyl Ester

생성물 1

HCID 536986381-(4-Nitro-benzyl)-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Benzyl Ester수율 33.2%

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 benzyl ester (1.733 g, 3.72 mmol), tributyltin methoxide (1.79 g, 1.6 ml, 5.58 mmol), isopropenyl acetate (0.56 g, 0.61 ml, 5.58 mmol), palladium (II) acetate (41.5 mg, 0.19 mmol) and tri-o-tolylphosphine (113 mg, 0.37 mmol) in toluene (5 ml) was heated at about 95° C. under nitrogen for about 6 hours. The reaction solution was cooled, concentrated in vacuo, and subjected to flash chromatography on silica (105 g, 30% ethyl acetate/hexanes). The partially pure product was re-chromatographed on silica (12 g, 50% methylene chloride/hexanes) to give the title compound (547 mg).

후처리

  1. temperatureThe reaction solution was cooled
  2. concentrationconcentrated in vacuo
  3. customThe partially pure product was re-chromatographed on silica (12 g, 50% methylene chloride/hexanes)

출처 및 근거

ORD 기록
ord-2b0d2fa772d247feaa191a73d162f935
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859044

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