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

HRID 2307916노트

반응식

HRID 2307916 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-3cf926484c394417b443da5113a6b4e4
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06833387B1

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