5-Bromo-3-methylisoquinoline → 5-Allyl-3-methylisoquinoline

HRID 2056856ノート

反応式

HRID 2056856 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9](Br)[CH:8]=[CH:7][CH:6]=2.[CH2:13]([CH:17]([Sn])C=C(CCCC)CCCC)[CH2:14]CC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:17]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([CH3:1])[N:3]=[CH:4]2)[CH:13]=[CH2:14]

参加物

5

反応物 2

HCID 218161685-Bromo-3-methylisoquinolineHCID 86589045Tributylallyltin

生成物 1

HCID 223376835-Allyl-3-methylisoquinoline

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Methyl-5-bromoisoquinoline (1.0 g, 4.5 mmol), tributylallyltin (1.6 mL, 5.0 mmol), and dichirobis(tri-o-tolylphosphine)palladium (II) were combined in toluene (100 mL) and refluxed for 14 hours. The mixture was cooled, diluted with ethyl acetate, and washed twice with aqueous NH4Cl. The organic phase was separated, concentrated, and the residue was purified by chromatography (ethyl acetate:hexanes, 30:70) to provide the title compound. 1H NMR (300 MHz, d6-DMSO) 9.21 (s, 1H), 8.00 (d, 1H), 7.63 (m, 2H), 7.58 (m, 1H), 4.18 (s, 2H), 3.62 (s, 3H), 2.62 (s 3H). MS (DCI/NH3) m/e 216 (M+H)+.

後処理

  1. temperaturerefluxed for 14 hours
  2. temperatureThe mixture was cooled
  3. washwashed twice with aqueous NH4Cl
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography (ethyl acetate:hexanes, 30:70)

出典と根拠

ORDレコード
ord-8350fe7c97ca43eba6a833eb92f7aadc
出典データセット
uspto-grants-2008_02
特許番号
US07335678B2

反応ノート

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