3,4-Dichlorobenzyl chloride → Methyl N-(3,4-dichlorobenzyl)-2-methoxycarbonyl-3-indoleacetate

HRID 2307916ノート

反応式

HRID 2307916 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Cl.[CH3:11][O:12][C:13]([C:15]1[NH:16][C:17]2[C:22]([C:23]=1[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:15]1[C:13]([O:12][CH3:11])=[O:14]

参加物

5

反応物 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 10332197methyl 3-(2-methoxy-2-oxoethyl)-1H-indole-2-carboxylate

生成物 1

HCID 54370673Methyl N-(3,4-dichlorobenzyl)-2-methoxycarbonyl-3-indoleacetate収率 65.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

3,4-Dichlorobenzyl chloride (8.2 g) was added to a stirred solution of methyl 2-methoxycarbonyl-3-indoleacetate (6.5 g) and potassium carbonate (8.36 g) in acetonitrile (200 ml) under an atmosphere of argon. The reaction was heated to 80° C. for 24 hours. The reaction was concentrated in vacuo and partitioned between ethyl acetate and water. Combined organic extracts were washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using 25% ethyl acetate:iso-hexane as eluent to give the product as a white solid (6.95 g, 65%), NMR d (CD3SOCD3) 3.60 (s, 3H), 3.77 (s, 3H), 4.13 (s, 2H), 5.89 (s, 2H), 6.89 (dd, 1H), 7.16 (t, 1H), 7.27 (d, 1H), 7.34 (t, 1H), 7.52 (d, 1H), 7.57 (d, 1H), 7.78 (d, 1H); M/z (+) 406 (MH+).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. washCombined organic extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-3cf926484c394417b443da5113a6b4e4
出典データセット
uspto-grants-2004_12
特許番号
US06833387B1

反応ノート

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