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

HRID 340121노트

반응식

HRID 340121 반응식
[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

참가 물질

4

반응물 2

HCID 6764936-BromoindoleHCID 53541824-Chloro B-nitrostyrene

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-9eea9c60d0994d89966ebd0874301eb2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895566B2

반응 노트

불러오는 중…