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Sodium Carbonate → HCID 18180219, 화합물

HRID 1383312
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HRID 1383312 반응식
[NH2:1][C:2]1[C:7](Br)=[N:6][CH:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=1B(O)O>C1C=CC=CC=1.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.C(O)C>[NH2:1][C:2]1[C:7]([C:21]2[CH:22]=[C:23]([Cl:27])[CH:24]=[C:25]([Cl:26])[C:20]=2[Cl:19])=[N:6][CH:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[N:3]=1
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 51065082,3,5-Trichlorophenylboronic acid3회HCID 18180200HCID 18180200, 화합물

생성물 1

HCID 18180219HCID 18180219, 화합물

시약·촉매·용매 3

HCID 241Benzene용매HCID 702Ethanol용매3회
HCID 178418397
HCID 178418397, 화합물
용매

실험 절차

A mixture of 2-amino-3-bromo-6-acetamidopyrazine (7.00 g, 0.03 mole) in benzene (60.90 ml) and tetrakis(triphenylphosphine)palladium(0) was stirred under nitrogen at room temperature for 10 minutes. 2M aqueous sodium carbonate (30.24 ml) was added to the mixture followed by a solution of 2,3,5-trichlorobenzene boronic acid (6.83 g, 0.03 mole) in absolute ethanol (7.07 ml) and the mixture refluxed under nitrogen for 17 hrs. A further equivalent of 2,3,5-trichlorobenzene boronic acid in absolute ethanol was then added and the mixture refluxed for an additional 7.50 hrs. Finally, another equivalent of 2,3,5-trichlorobenzene boronic acid in absolute ethanol was added to the mixture and continued refluxing for 17 hrs. The cooled mixture was evaporated in vacuo. The residue was dissolved in chloroform (150 ml), washed with aqueous saturated sodium bicarbonate (1×100 ml) and water (1×100 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated down in vacuo. The residue was purified by ‘flash chromatography’ using chloroform to 98:2 chloroform:methanol as the eluent. Yield 3.02 g (30%), M.p. 200-203° C.

후처리

  1. temperaturethe mixture refluxed under nitrogen for 17 hrs
  2. temperaturethe mixture refluxed for an additional 7.50 hrs
  3. temperaturecontinued refluxing for 17 hrs
  4. customThe cooled mixture was evaporated in vacuo
  5. dissolutionThe residue was dissolved in chloroform (150 ml)
  6. washwashed with aqueous saturated sodium bicarbonate (1×100 ml) and water (1×100 ml)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customthe filtrate evaporated down in vacuo
  10. customThe residue was purified by ‘flash chromatography’

출처 및 근거

ORD 기록
ord-aa974e05bdff498aa05a03f303a76cf6
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06255307B1

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