Sodium Carbonate → HCID 58894567, 화합물

HRID 1028355

반응식

HRID 1028355 반응식
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:23]=[CH:22][C:21]([N:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(#N)C>[CH3:8][C:7]1[C:2]([C:34]2[CH:33]=[CH:32][C:31]([N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]3[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=3)=[CH:36][CH:35]=2)=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 11639307Diphenyl-(4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenyl)-amineHCID 116726802-Chloro-3,5-dimethylpyrazine

생성물 1

HCID 58894567HCID 58894567, 화합물수율 30%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

Next, there were put 0.36 g of 2-chloro-3,5-dimethylpyrazine, 0.92 g of 4,4,5,5-tetramethyl-2-(4-diphenylaminophenyl)-1,3,2-dioxaborolane obtained in Step 1, 0.26 g of sodium carbonate, 0.011 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile in a recovery flask equipped with a reflux pipe. The air in the flask was replaced by argon. This reaction container was heated by microwave irradiation (2.45 GHz, 100 W) for 20 minutes. After that, the reaction container was cooled to 50° C. or lower, water was added to the reaction solution, and the organic layer was subjected to extraction with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled, and the obtained residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and ethyl acetate as a developing solvent, thereby obtaining the objective pyrazine derivative Hdmdpappr (white powder, 30% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 2 is shown by (b-2).

후처리

  1. customequipped with a reflux pipe
  2. temperatureThis reaction container was heated by microwave irradiation (2.45 GHz, 100 W) for 20 minutes
  3. extractionthe organic layer was subjected to extraction with dichloromethane
  4. washThe obtained organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter the drying, the solution was filtered
  7. distillationThe solvent of this solution was distilled
  8. customthe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3a6140d3fe854b9198a2aff6441ddd64
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735581B2

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