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alpha-Bromo-o-chlorotoluene → (4-benzyl-4-hydroxy-piperidin-1-yl)-[1-(2-chloro-benzyl)-2-methyl-1H-indol-3-yl]-methanone

HRID 505084
ノート
印刷プレビュー

反応式

HRID 505084 の反応式
[CH2:1]([C:8]1([OH:26])[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH3:25])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:37]>CN(C=O)C>[CH2:1]([C:8]1([OH:26])[CH2:9][CH2:10][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[C:17]=2[CH3:25])=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 24758Sodium hydrideHCID 66744648(4-benzyl-4-hydroxy-piperidin-1-yl)-(2-methyl-1H-indol-3-yl)-methanone

生成物 1

HCID 59429625(4-benzyl-4-hydroxy-piperidin-1-yl)-[1-(2-chloro-benzyl)-2-methyl-1H-indol-3-yl]-methanone収率 63.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 40 mg (0.11 mmol) of (4-benzyl-4-hydroxy-piperidin-1-yl)-(2-methyl-1H-indol-3-yl)-methanone in 5 ml DMF were added 5 mg (0.11 mmol) NaH (60% in oil). The mixture was stirred at RT for 30 min. and then 28 mg (0.13 mmol) of 1-bromomethyl-2-chloro-benzene were added. The mixture was stirred an additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Preparative HPLC (30% CH3CN/H2O) afforded 33 mg (61%) of (4-benzyl-4-hydroxy-piperidin-1-yl)-[1-(2-chloro-benzyl)-2-methyl-1H-indol-3-yl]-methanone as a white solid.

後処理

  1. stirringThe mixture was stirred an additional hour
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-139efdfcfa5149de81f9f9bee22483ee
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07781436B2

反応ノート

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