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

HRID 914990ノート

反応式

HRID 914990 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7263c587ce444de1ae78eb86f7fdb86f
出典データセット
uspto-grants-2007_09
特許番号
US07265122B2

反応ノート

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