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Sodium Carbonate → HCID 21830737、化合物

HRID 1600931
ノート
印刷プレビュー

反応式

HRID 1600931 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 10340Sodium CarbonateHCID 8536523-bromo-N-phenylbenzamideHCID 2724141Tetrabutylammonium FluorideHCID 21717159HCID 21717159、化合物

生成物 1

HCID 21830737HCID 21830737、化合物収率 11.8%

試薬・触媒・溶媒 5

HCID 178418397
HCID 178418397、化合物
触媒
HCID 702Ethanol溶媒
HCID 1140Toluene溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b145db7797f948bf9d93d8b542ee30d9
出典データセット
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05977105

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート