Phenylboronic Acid → 2-acetamido-N-((5-phenyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamide

HRID 623660노트

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HRID 623660 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][N:27]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[C:16](Br)[CH:17]=1)=[O:9])(=[O:3])[CH3:2].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.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:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][N:27]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[C:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:17]=1)=[O:9])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 675096872-acetamido-N-((5-bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamide

생성물 1

HCID 675083942-acetamido-N-((5-phenyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamide수율 30%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of 2-acetamido-N-((5-bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamide (20 mg, 0.05 mmol, Step-1), phenylboronic acid (11 mg, 0.09 mmol), tetrakis(triphenylphosphine)palladium (3 mg, 2.2 microM) in dioxane (2 mL) is added saturated aqueous sodium hydrogencarbonate (0.4 mL). The mixture is heated at 100° C. for 1 hr. After cooled to room temperature, the mixture is extracted with ethyl acetate, dried over sodium sulfate. The organic solvent is removed under reduced pressure. The residue is purified by short column chromatography on amine gel eluting with ethylacetate, and then purified by preparative LC-MS to give 6 mg (30% yield) of the title compound.

후처리

  1. temperatureAfter cooled to room temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe organic solvent is removed under reduced pressure
  5. customThe residue is purified by short column chromatography on amine gel
  6. washeluting with ethylacetate
  7. custompurified by preparative LC-MS

출처 및 근거

ORD 기록
ord-e3a7e2a9a0f6446e9be6940130e82e8f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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