Benzene, 1-bromo-3-nitro- → 2-[3-(3-Nitrophenyl)prop-2-ynyl]-1,2,3,4-tetrahydroisoquinoline

HRID 914990노트

반응식

HRID 914990 반응식
[CH2:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)[C:2]#[CH:3].Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1>C(N(CC)CC)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:21]([C:17]1[CH:16]=[C:15]([C:3]#[C:2][CH2:1][N:4]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5]2)[CH:20]=[CH:19][CH:18]=1)([O-:23])=[O:22]

참가 물질

6

반응물 2

HCID 11457Benzene, 1-bromo-3-nitro-HCID 143412942-(Prop-2-yn-1-yl)-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 589582322-[3-(3-Nitrophenyl)prop-2-ynyl]-1,2,3,4-tetrahydroisoquinoline수율 66.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

반응 조건

온도
90 °C

실험 절차

To a solution of 81 (2.06 g, 10.2 mmol) in anhydrous triethylamine (30 mL) were sequentially added 1-bromo-3-nitrobenzene (1.83 g, 10.67 mmol), CuI (0.39 g, 2.05 mmol) and Pd(PPh3)4 (1.17 g, 1.0 mmol). The mixture was heated at 90° C. for 1 hour before it was filtered through Celite® and the filtrate was diluted with EtOAc (150 mL). The resulting solution was washed with water (100 mL), brine (100 mL), dried over Na2SO4 and concentrated. The residue was purified via flash silica gel chromatography to provide 93 (1.97 g, 66%).

후처리

  1. filtrationwas filtered through Celite®
  2. additionthe filtrate was diluted with EtOAc (150 mL)
  3. washThe resulting solution was washed with water (100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified via flash silica gel chromatography

출처 및 근거

ORD 기록
ord-7263c587ce444de1ae78eb86f7fdb86f
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265122B2

반응 노트

불러오는 중…