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Boron tribromide → 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

HRID 1357276
ノート
印刷プレビュー

反応式

HRID 1357276 の反応式
B(Br)(Br)Br.[Br:5][C:6]1[C:15]([O:16]C)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH2:18][N:19]([CH3:32])[C:20]([C:22]1[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=1)=[O:21])=[CH:11]2.C(=O)=O.CC(C)=O>C(Cl)Cl>[Br:5][C:6]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH2:18][N:19]([CH3:32])[C:20]([C:22]1[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=1)=[O:21])=[CH:11]2
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 25134Boron tribromideHCID 18522661Acetone cardice2 回HCID 865873911-methyl-1H-indole-3-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide

生成物 1

HCID 865873931-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide収率 84.4%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

実験手順

A solution of 1.0 M boron tribromide in methylene chloride (55.0 mL, 54.9 mmol) in 50 mL of methylene chloride was added under nitrogen dropwise over 1.5 h to a solution of 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide (8.0 g, 18.3 mmol), prepared in the previous step, in 300 mL of methylene chloride at dry ice-acetone temperature. The dry ice-acetone bath was replaced with an ice bath immediately after the addition. The reaction stirred at ice bath temperature for 2 h. At ice bath temperature, the reaction was quenched by the dropwise with water. The reaction was partitioned between methylene chloride and water. A solid formed in the organic layer and was collected by filtration. The solid was dried under reduced pressure to give 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (6.5359 g, 84%) as a white solid, mp 189-190° C.

後処理

  1. additionimmediately after the addition
  2. customAt ice bath temperature, the reaction was quenched by the dropwise with water
  3. customThe reaction was partitioned between methylene chloride and water
  4. customA solid formed in the organic layer
  5. filtrationwas collected by filtration
  6. customThe solid was dried under reduced pressure

出典と根拠

ORDレコード
ord-3768de337ac049d492a3b7cce662cbef
出典データセット
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06589970B2

反応ノート

読み込み中…

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