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

HRID 2361358ノート

反応式

HRID 2361358 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-db4c5c9ed2604de7a4172fbe64095eb5
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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