6-Bromoindole → 6-bromo-3-(1-(4-chlorophenyl)-2-nitroethyl)-1H-indole

HRID 521361ノート

反応式

HRID 521361 の反応式
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)([O-:3])=[O:2].[Br:13][C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[CH:19][NH:20]2)=[CH:16][CH:15]=1>CO>[Br:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([CH:5]([C:6]3[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=3)[CH2:4][N+:1]([O-:3])=[O:2])=[CH:19][NH:20]2)=[CH:16][CH:15]=1

参加物

4

反応物 2

HCID 6764936-BromoindoleHCID 53541824-Chloro B-nitrostyrene

生成物 1

HCID 674367186-bromo-3-(1-(4-chlorophenyl)-2-nitroethyl)-1H-indole収率 45.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

1-((1E)-2-Nitrovinyl)-4-chlorobenzene (0.206 g, 1.12 mmol) was added to a solution of 6-bromoindole (0.200 g, 1.02 mmol) in methanol (5 mL), followed by the addition of sufamic acid (39.6 mg, 0.40 mmol). The mixture was stirred at 80° C. for 16 hours. The mixture was concentrated then diluted with EtOAc (15 mL) and washed with H2O (15 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with EtOAc/hexane (0-50%) to give 6-bromo-3-(1-(4-chlorophenyl)-2-nitroethyl)-1H-indole (0.175 g, 45.2%). 1H NMR (CDCl3, 400 MHz) δ 8.12 (s, 1H), 7.51 (s, 1H), 7.28 (d, J=8.5 Hz, 2H), 7.25-7.20 (m, 3H), 7.17 (d, J=8.5 Hz, 1H), 7.15 (s, 1H), 5.12 (t, 1H), 5.01 (q, 1H), 4.88 (q, 1H).

後処理

  1. concentrationThe mixture was concentrated
  2. additionthen diluted with EtOAc (15 mL)
  3. washwashed with H2O (15 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with EtOAc/hexane (0-50%)

出典と根拠

ORDレコード
ord-88bf2e11d6944174b0a9c350cb6bd64e
出典データセット
uspto-grants-2016_05
特許番号
US09328091B2

反応ノート

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