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

HRID 585969노트

반응식

HRID 585969 반응식
[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]

참가 물질

5

반응물 2

HCID 218161685-Bromo-3-methylisoquinolineHCID 86589045Tributylallyltin

생성물 1

HCID 223376835-Allyl-3-methylisoquinoline

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

3-Methyl-5-bromoisoquinoline (1.0 g, 4.5 mmol), tributylallyltin (1.6 mL, 5.0 mmol), and dichlrobis(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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f5d6ca98a5374e2495744cfd08950dbf
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933311B2

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