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Boron tribromide → Methyl 4-[(5,6-dichloro-2-{[4-(hydroxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

HRID 1594522
ノート
印刷プレビュー

反応式

HRID 1594522 の反応式
[Cl:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]2[N:6]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[C:7](=[N:10][C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[N:8]([CH3:9])[C:4]=2[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]2[N:6]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[C:7](=[N:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:8]([CH3:9])[C:4]=2[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 69418089Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

生成物 1

HCID 69418442Methyl 4-[(5,6-dichloro-2-{[4-(hydroxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To the title compound of Example 19 Step C (0.11 mmol, 50 mg) in CH2Cl2 (0.5 mL) cooled to −78° C. was added dropwise BBr3 (0.33 mol, 330 μL of a 1 M solution in CH2Cl2). After addition, the reaction was removed from the cold bath for 30 min, then cooled to −78° C. and diluted with MeOH. The mixture was concentrated under reduced pressure and the product was isolated by chromatography on silica eluting with 4% MeOH in CH2Cl2 as a white solid. LC-MS (ESI, Method B): 1.80 min, m/z 456.1 (M+1).

後処理

  1. additionAfter addition
  2. customthe reaction was removed from the cold bath for 30 min
  3. additiondiluted with MeOH
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe product was isolated by chromatography on silica eluting with 4% MeOH in CH2Cl2 as a white solid
  6. custom1.80 min, m/z 456.1 (M+1)

出典と根拠

ORDレコード
ord-0ed1f94ebad9404ca693e12e11583ad4
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07301036B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート