Sodium Carbonate → ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

HRID 508095ノート

反応式

HRID 508095 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N:8]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-:37])=[O:36])(=[O:28])=[O:27])[CH:9]2[C:17]3[C:12](=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].[Si:45]([O:52][C:53]1[CH:58]=[C:57]([CH3:59])[C:56](B(O)O)=[C:55]([CH3:63])[CH:54]=1)([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C.C1(C)C=CC=CC=1.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>[Si:45]([O:52][C:53]1[CH:58]=[C:57]([CH3:59])[C:56]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[CH2:11][CH2:10][CH:9]3[N:8]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-:37])=[O:36])(=[O:28])=[O:27])[C:6]2[CH:5]=[CH:4][C:3]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:2]([F:1])[CH:7]=2)=[C:55]([CH3:63])[CH:54]=1)([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 23157502HCID 23157502、化合物HCID 598383324-[(Tert-butyldimethylsilyl)oxy]-2,6-dimethylphenylboronic acid

生成物 1

HCID 68720751ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

Ethyl 3-{2-fluoro-4-[[(2-nitrophenyl)sulfonyl](4-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1H-inden-1-yl)amino]phenyl}propanoate (3.14 g, 4.76 mmol), (4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)boronic acid (2.0 g, 7.14 mmol) and sodium carbonate (1.51 g, 14.3 mmol) were dissolved in a mixture of water (10 mL), ethanol (10 mL) and toluene (30 mL), and the air was substituted with argon gas. Tetrakis(triphenylphosphine)palladium(0) (0.275 g, 0.24 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 120° C. for 16 hr. After cooling, the reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3%-60% ethyl acetate/hexane) to give ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate as a yellow oil. The obtained oil was dissolved in tetrahydrofuran (30 mL), tetrabutylammonium fluoride (1 M THF solution, 2.43 mL, 2.43 mmol) was added under stirring at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-60% ethyl acetate/hexane) to give the title compound (1.46 g, yield 78%, 2 steps) as a yellow oil.

後処理

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (3%-60% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-d24875c9c7cf49108b3d3f90b03fdcfe
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

読み込み中…