Sodium Carbonate → 5-Furan-3-yl-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 559790노트

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HRID 559790 반응식
I[C:2]1[CH:3]=[C:4]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[O:21])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8].[O:34]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35]1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[CH3:33][S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:20]([C:4]2[C:5](=[O:19])[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[C:7]([CH3:8])=[C:2]([C:36]3[CH:37]=[CH:38][O:34][CH:35]=3)[CH:3]=2)=[O:21])=[CH:25][CH:26]=1)(=[O:32])=[O:31]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acid2회HCID 115199335-Iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoro-methyl)phenyl]1,2-dihydropyridine-3-carboxamide

생성물 1

HCID 667253515-Furan-3-yl-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide수율 62%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매2회HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A mixture of 5-iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (Example 1 (d), 0.0413 g, 0.07 mmol), furan-3-boronic acid (0.009 g, 0.08 mmol), Pd(PPh3)4 (0.004 g, 3.46 nmol), DME (2 ml) and Na2CO3 (2 ml, 2M) was vigorously stirred under nitrogen in a sealed vial at 80° C. for 2 h. Another portion of furan-3-boronic acid (0.005 g) and Pd(PPh3)4 (0.004 g) was added and the reaction was allowed to go for another hour. The mixture was allowed to cool, and was then partitioned between EtOAc and water. The organic phase was collected and the aqueous phase was extracted with another portion of EtOAc (10 ml). The combined organic phases were washed with water, brine, and dried over Na2SO4. Filtration and evaporation gave a crude oil which was purified on silica (heptane:EtOAc 2:1 to 1:1 to 1:2), which after evaporation of pure fractions gave 0.023 g (62%) of the title compound as a white solid.

후처리

  1. waitto go for another hour
  2. temperatureto cool
  3. customwas then partitioned between EtOAc and water
  4. customThe organic phase was collected
  5. extractionthe aqueous phase was extracted with another portion of EtOAc (10 ml)
  6. washThe combined organic phases were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration and evaporation
  9. customgave a crude oil which
  10. customwas purified on silica (heptane:EtOAc 2:1 to 1:1 to 1:2), which
  11. customafter evaporation of pure fractions

출처 및 근거

ORD 기록
ord-99bda83e6fc1450390008231da4e64ed
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063073B2

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