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

HRID 342800

反応式

HRID 342800 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

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 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).

後処理

  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)

出典と根拠

ORDレコード
ord-2b0d2fa772d247feaa191a73d162f935
出典データセット
uspto-grants-1999_01
特許番号
US05859044

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