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Benzyl Bromide → 1-Benzyloxy-7-chloro-6-fluoro-isoquinoline

HRID 38445
ノート
印刷プレビュー

反応式

HRID 38445 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[F:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(OCC)(=O)C>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH2:14]([O:12][C:9]1[C:10]2[C:5](=[CH:4][C:3]([F:13])=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 7498Benzyl Bromide2 回HCID 8857Ethyl AcetateHCID 598182487-Chloro-6-fluoroisoquinolin-1(2H)-one

生成物 1

HCID 598182521-Benzyloxy-7-chloro-6-fluoro-isoquinoline

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

7-Chloro-6-fluoro-2H-isoquinolin-1-one (prepared according to WO 2007/012422; 52.2 g) was dissolved in THF (1 L). After addition of silver carbonate (145.5 g) and benzyl bromide (40.6 mL), the mixture was stirred at room temperature overnight. Another 6.2 mL of benzyl bromide were added and the mixture was stirred at 70° C. for 2 h. After cooling down to room temperature, the reaction mixture was diluted by addition of 1 L of ethyl acetate and filtered over celite. The filter cake was washed thoroughly, the organic layer was evaporated and subjected to silica gel chromatography (n-heptanes: methyl tert. butyl ether) to give 27.8 g of the title compound 1. Rt=3.73 min (Method 1). Detected mass: 288.1 (M+H+).

後処理

  1. stirringthe mixture was stirred at 70° C. for 2 h
  2. temperatureAfter cooling down to room temperature
  3. filtrationfiltered over celite
  4. washThe filter cake was washed thoroughly
  5. customthe organic layer was evaporated

出典と根拠

ORDレコード
ord-220f33ef87d748ec8a5acb8f081f3744
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524737B2

反応ノート

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