Toluene → HCID 69156765, 화합물

HRID 750148노트

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HRID 750148 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].[S:33]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34]1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C(O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:35]1[CH:36]=[CH:37][S:33][CH:34]=1)=[CH:10][CH:9]=2)=[O:4]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 10239063HCID 10239063, 화합물

생성물 1

HCID 69156765HCID 69156765, 화합물수율 86.1%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), 3-thiopheneboronic acid (120 mg), tetrakis(triphenylphosphine)palladium(0) (35 mg), toluene (6 ml), ethanol (0.8 ml) and 2M aqueous sodium carbonate solution (0.8 ml) was heated under reflux under a nitrogen atmosphere for 6 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The solvent was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) and recrystallized (ethyl acetate-hexane) to give the title compound (260 mg).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux under a nitrogen atmosphere for 6 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialThe solvent was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1)
  8. customrecrystallized (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-bf539ddad86444d4b913c7469a69c00c
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402595B2

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