Water → Methyl 3-[4-({[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-phenyl]-acrylate

HRID 416208ノート

反応式

HRID 416208 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=2)=[CH:2]1.C(N(C(C)C)CC)(C)C.Br[CH2:36][CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].O>CS(C)=O>[C:42]([Si:39]([CH3:41])([CH3:40])[O:38][CH2:37][CH2:36][N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=1)[CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)([CH3:45])([CH3:44])[CH3:43]

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 59036879Methyl 3-(4-{[2-(1H-indol-3-yl)-ethylamino]-methyl}-phenyl)-acrylate

生成物 1

HCID 59036876Methyl 3-[4-({[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-phenyl]-acrylate収率 97.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
52.5 °C

実験手順

To a stirred solution of 2 (2.82 g, 8.44 mmol) and diisopropylethylamine (2.21 mL, 12.66 mmol) in anhydrous DMSO (22 mL) at room temperature under nitrogen was added (2-bromo-ethoxy)-tert-butyl-dimethylsilane (2.17 mL, 10.12 mmol). The reaction mixture was heated at 50-55° C. for 24 h, poured into water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2, 15/85, plus a few drops of NH4OH) to afford the title compound 3 (4.06 g, 8.24 mmol, 97% yield) as a dark orange oil.

後処理

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2, 15/85, plus a few drops of NH4OH)

出典と根拠

ORDレコード
ord-1890850da9a748f18d63f8d7eb234db6
出典データセット
uspto-grants-2012_01
特許番号
US08088805B2

反応ノート

読み込み中…