Potassium Carbonate → HCID 66974560, 화합물

HRID 1962652노트

반응식

HRID 1962652 반응식
C(OC(=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([S:21]([C:24]2[CH:25]=[N:26][CH:27]=[C:28](Br)[CH:29]=2)(=[O:23])=[O:22])[CH:11]=1)[CH3:8])(C)(C)C.[CH3:32]B(O)O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+].C(OCC)(=O)C.[ClH:53]>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.O1CCOCC1>[ClH:53].[ClH:53].[CH3:8][NH:7][CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([S:21]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH3:32])[CH:29]=2)(=[O:22])=[O:23])[CH:11]=1

참가 물질

9

반응물 5

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974640HCID 66974640, 화합물

생성물 1

HCID 66974560HCID 66974560, 화합물수율 39%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

Under an argon atmosphere, a mixture of tert-butyl({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (112 mg), methylboronic acid (18 mg), tetrakis(triphenylphosphine)palladium (23 mg), potassium carbonate (138 mg) and 1,4-dioxane (5 mL) was stirred at 80° C. for one day. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1) to give an oil. The oil was dissolved in ethanol (1 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added. After stirring at room temperature for 1 hr, the mixture was concentrated under reduced pressure. The residue was recrystallized from ethanol-ethyl acetate to give the title compound as a colorless solid (yield 32.6 mg, 39%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1)
  6. customto give an oil
  7. stirringAfter stirring at room temperature for 1 hr
  8. concentrationthe mixture was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethanol-ethyl acetate

출처 및 근거

ORD 기록
ord-843579c2b0384f3f91393fb9e2a8c606
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415368B2

반응 노트

불러오는 중…