Isobutylene → HCID 70496137、化合物

HRID 2408137ノート

反応式

HRID 2408137 の反応式
[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.[CH2:26]=[C:27]([CH3:29])[CH3:28].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.C(OCC)(=O)C>[Br:17][C:18]1[CH:19]=[C:20]([CH:21]2[CH2:26][C:27]([CH3:29])([CH3:28])[C:12]3[C:13](=[CH:14][CH:15]=[C:10]([S:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)(=[O:9])=[O:8])[CH:11]=3)[NH:16]2)[CH:23]=[CH:24][CH:25]=1

参加物

7

反応物 4

HCID 8255IsobutyleneHCID 765833-BromobenzaldehydeHCID 2107944-(Morpholinosulfonyl)anilineHCID 2733225Ytterbium triflate

生成物 1

HCID 70496137HCID 70496137、化合物収率 47.4%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 4-(morpholine-4-sulfonyl)-phenylamine (3 g, 12.4 mmol) and 3-bromo-benzaldehyde (2.52 g, 13.6 mmol) in acetonitrile (150 mL) were added isobutene (2.7 mL, 37.2 mmoll) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (1.54 g, 2.5 mmol). The resulting mixture was stirred at 80° C. for 18 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-40% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4-dimethyl-6-(morpholine-4-sulfonyl)-1,2,3,4-tetrahydro-quinoline (2.7 g, 47.4%) as a light yellow solid: MS (ESI) M+1=465.0 & 467.0.

後処理

  1. washwashed with water (100 mL×2) and brine (100 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 10-40% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-7cd534a5f6a748dca3d5ad0d9fb35dd2
出典データセット
uspto-grants-2014_08
特許番号
US08809369B2

反応ノート

読み込み中…