Ethanol → 2-Methyl-1'H,2H-3,4'-bipyrazole

HRID 238370노트

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HRID 238370 반응식
I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.C(OC([N:15]1[CH:19]=[C:18](B(O)O)[CH:17]=[N:16]1)=O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>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.C1(C)C=CC=CC=1>[CH3:7][N:6]1[C:2]([C:18]2[CH:19]=[N:15][NH:16][CH:17]=2)=[CH:3][CH:4]=[N:5]1

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 133340655-Iodo-1-methyl-1H-pyrazoleHCID 441186751-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acid

생성물 1

HCID 1363877762-Methyl-1'H,2H-3,4'-bipyrazole수율 32.9%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (750 mg), [1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl]boronic acid (1.27 g), tetrakis(triphenylphosphine)palladium(0) (209 mg), 2 M sodium carbonate aqueous solution (3.6 mL), ethanol (3.6 mL) and toluene (7.2 mL) was stirred at 100° C. for 14 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=4:1 to 0:10), so as to obtain the title compound (176 mg) in the form of a light yellow solid.

후처리

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationwas then concentrated under a reduced pressure
  4. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=4:1 to 0:10)

출처 및 근거

ORD 기록
ord-a540602f3ca5468981ff4c7803c95013
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642626B2

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