反応式
F[B-](F)(F)F.C(C1C=CC=C(C(C)C)C=1[N+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[C:46]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:47]=1[CH:48]=[CH:49][N:50]2[S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56].[C:64]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])(=[O:66])[CH3:65]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:58]1([S:55]([N:50]2[C:51]3[C:47](=[C:46]([CH2:65][C:64]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH:54]=[CH:53][CH:52]=3)[CH:48]=[CH:49]2)(=[O:57])=[O:56])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
To a mixture of 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium tetrafluoroborate (94 mg, 0.196 mmol), tris(dibenzylideneacetone)dipalladium (180 mg, 0.196 mmol), and lithium bis(trimethylsilyl)amide (1.37 M in t-BuOMe, 11.0 mL, 15.1 mmol) were added 4-bromo-1-(phenylsulfonyl)-1H-indole from Step A (2.20 g, 6.54 mmol), tert-butyl acetate (988 mg, 8.51 mmol), and toluene (15 mL). The resulting mixture was stirred at ambient temperature for 18 h then partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (30 mL). The organic layer was washed with brine, then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 85:15, to give the title compound. MS: m/z=316 (M−C4H7).
後処理
- customthen partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (30 mL)
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by silica gel chromatography
- washeluting with a gradient of hexane
出典と根拠
- ORDレコード
- ord-2e1587af39ff4af1999cdfdc5f2eaadb
- 出典データセット
- uspto-grants-2012_03
- 特許番号
- US08133891B2
関連ノート
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