6-Bromoindole → Benzyl 3-(1-(6-bromo-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate

HRID 2361358노트

반응식

HRID 2361358 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11][C:12]1[C:17](/[CH:18]=[CH:19]/[N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C.CCCCCC>C1COCC1.CN1C(=O)CCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:18]([C:17]3[C:12]([CH3:11])=[C:13]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:14]=[CH:15][CH:16]=3)[CH2:19][N+:20]([O-:22])=[O:21])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 6764936-BromoindoleHCID 21226206Ethyl acetate hexaneHCID 67995173(E)-Benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate

생성물 1

HCID 67994880Benzyl 3-(1-(6-bromo-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate수율 61.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
120 °C

실험 절차

A mixture of 6-bromo-1H-indole (2.82 g, 14.41 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (3.0 g, 9.61 mmol) was dissolved in THF (50 mL) and NMP (0.5 mL). The THF was removed under vacuum, and the residue was heated at 120° C. for 16 hr and then at 125° C. for 6 hr. Upon cooling to room temperature, the mixture was dissolved in THF (50 mL). The resulting solution was diluted with ethyl acetate (250 mL), washed with water (3×80 mL) and brine (60 mL), and dried over anhydrous MgSO4. The desired product (3.00 g, 5.90 mmol, 61.4% yield) was isolated as a beige solid by ISCO (300 g silica gel, 25-60 ethyl acetate/hexane).

후처리

  1. customThe THF was removed under vacuum
  2. temperatureUpon cooling to room temperature
  3. dissolutionthe mixture was dissolved in THF (50 mL)
  4. additionThe resulting solution was diluted with ethyl acetate (250 mL)
  5. washwashed with water (3×80 mL) and brine (60 mL)
  6. dry with materialdried over anhydrous MgSO4

출처 및 근거

ORD 기록
ord-db4c5c9ed2604de7a4172fbe64095eb5
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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