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Sodium Carbonate → HCID 21830737, 화합물

HRID 1600931
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인쇄 미리보기

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HRID 1600931 반응식
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][CH:31]([O:43][Si](C(C)(C)C)(C)C)[CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=2)[CH:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].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(O)C.C1(C)C=CC=CC=1>[C:14]1([NH:13][C:11]([C:10]2[CH:9]=[C:8]([C:37]3[CH:36]=[CH:35][C:34]([O:33][CH2:32][CH:31]([OH:43])[CH2:30][CH2:29][C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)=[CH:39][CH:38]=3)[CH:22]=[CH:21][CH:20]=2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
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참가 물질

10

반응물 4

HCID 10340Sodium CarbonateHCID 8536523-bromo-N-phenylbenzamideHCID 2724141Tetrabutylammonium FluorideHCID 21717159HCID 21717159, 화합물

생성물 1

HCID 21830737HCID 21830737, 화합물수율 11.8%

시약·촉매·용매 5

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매
HCID 8028Tetrahydrofuran용매
HCID 57417360Sodium chloride; water용매

반응 조건

온도
120 °C

실험 절차

Prepared according to the method described in Example 33a) from toluene (3 ml), aqueous sodium carbonate (2 M, 0.9 ml), ethanol (1.0 ml), 3-bromo-N-phenylbenzamide (0.48 g), (±)-4-[4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butoxy]benzeneboronic acid (0.7 g) and tetrakis(triphenylphosphine)palladium(0) (50 mg) with heating at 120° C. for 5 hours. The residue obtained after work up was purified by column chromatography over silica eluting with ethyl acetate:hexane (1:1) to give a colourless oil which was desilylated by treatment with tetrabutylammonium fluoride (0.7 ml; 1 M in tetrahydrofuran) in tetrahydrofuran at 0° C. After stirring at this temperature for 5 minutes a saturated solution of brine (5 ml) was added and the organic phase separated. The aqueous phase was extracted with ethyl acetate (20 ml). The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (1:19) to give the title compound as a colourless solid (0.09 g).

후처리

  1. customPrepared
  2. customThe residue obtained after work
  3. customup was purified by column chromatography over silica eluting with ethyl acetate:hexane (1:1)
  4. customto give a colourless oil which
  5. additionwas added
  6. customthe organic phase separated
  7. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (1:19)

출처 및 근거

ORD 기록
ord-b145db7797f948bf9d93d8b542ee30d9
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05977105

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