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Cesium carbonate → 5-(3-(tert-butylcarbamoyl)-5-nitrophenyl)-2-(4-fluorophenyl)-N-methyl-6-nitrobenzofuran-3-carboxamide

HRID 57756
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HRID 57756 반응식
FC(F)(F)S(O[C:7]1[C:8]([N+:27]([O-:29])=[O:28])=[CH:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[C:12]([C:22](=[O:25])[NH:23][CH3:24])[C:11]=2[CH:26]=1)(=O)=O.[C:32]([NH:36][C:37]([C:39]1[CH:40]=[C:41](B(O)O)[CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.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:32]([NH:36][C:37]([C:39]1[CH:40]=[C:41]([C:7]2[C:8]([N+:27]([O-:29])=[O:28])=[CH:9][C:10]3[O:14][C:13]([C:15]4[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=4)=[C:12]([C:22]([NH:23][CH3:24])=[O:25])[C:11]=3[CH:26]=2)[CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)=[O:38])([CH3:35])([CH3:33])[CH3:34]
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참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 44886943(3-(tert-Butylcarbamoyl)-5-nitrophenyl)boronic acidHCID 592753912-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl trifluoromethanesulfonate

생성물 1

HCID 902805835-(3-(tert-butylcarbamoyl)-5-nitrophenyl)-2-(4-fluorophenyl)-N-methyl-6-nitrobenzofuran-3-carboxamide수율 75.7%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

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온도
99 °C

실험 절차

To a mixture of 2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl trifluoromethanesulfonate (400 mg), (3-(tert-butylcarbamoyl)-5-nitrophenyl)boronic acid (345 mg) and Cs2CO3 (846 mg) in dioxane (8 mL) and water (1.5 mL) was added tetrakis(triphenylphosphine)palladium(0) (150 mg). The mixture was flushed with nitrogen and then heated at 99° C. for 16 hours. The mixture was diluted with water and extracted with EtOAc (2×100 mL). The organic layers were combined, washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column (hexanes/EtOAc=3:1) to give 5-(3-(tert-butylcarbamoyl)-5-nitrophenyl)-2-(4-fluorophenyl)-N-methyl-6-nitrobenzofuran-3-carboxamide 2 (350 mg).

후처리

  1. customThe mixture was flushed with nitrogen
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc (2×100 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column (hexanes/EtOAc=3:1)

출처 및 근거

ORD 기록
ord-00afd8b074ad48938f467461da35454d
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434738B2

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