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Ethanol → 6-Fluoro-3-[4-(4-iodo-3-methoxy-phenyl)-1,2,3-triazol-1-yl]-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 2035700
ノート
印刷プレビュー

反応式

HRID 2035700 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([I:9])=[C:5]([O:10][CH3:11])[CH:4]=1)#[CH:2].[N:12]([CH:15]1[CH2:21][CH2:20][C:19]2[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:18]=2[NH:17][C:16]1=[O:27])=[N+:13]=[N-:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].CCO>ClCCl.O.CN(C=O)C>[F:26][C:22]1[C:19]2[CH2:20][CH2:21][CH:15]([N:12]3[CH:2]=[C:1]([C:3]4[CH:8]=[CH:7][C:6]([I:9])=[C:5]([O:10][CH3:11])[CH:4]=4)[N:14]=[N:13]3)[C:16](=[O:27])[NH:17][C:18]=2[CH:25]=[CH:24][CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 702EthanolHCID 190256673-Azido-6-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 23667548Sodium AscorbateHCID 866614654-Ethynyl-1-iodo-2-methoxybenzene

生成物 1

HCID 666838136-Fluoro-3-[4-(4-iodo-3-methoxy-phenyl)-1,2,3-triazol-1-yl]-1,3,4,5-tetrahydro-1-benzazepin-2-one収率 95.1%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒

実験手順

4-Ethynyl-1-iodo-2-methoxy-benzene (22.23 g, 86 mmol), 3-azido-6-fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one (20.87 g, 95 mmol), and sodium ascorbate (15.69 g, 86 mmol) were added to EtOH (155 mL) and DMF (155 mL). CuSO4.5H2O (10.75 g, 43.1 mmol) was added to 20 mL water and added dropwise to the stirring reaction mixture. The reaction stirred for 17 hrs at room temp. Dichloromethane was added and the organic layer was washed with 2N NaOH, dried with sodium sulfate and concentrated. Purification on silica gel (dichloromethane:methanol, 1-15%). 6-Fluoro-3-[4-(4-iodo-3-methoxy-phenyl)-1,2,3-triazol-1-yl]-1,3,4,5-tetrahydro-1-benzazepin-2-one (39.1 g) was obtained as a colorless solid and carried on the next step.

後処理

  1. additionadded dropwise to the stirring reaction mixture
  2. washthe organic layer was washed with 2N NaOH
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customPurification on silica gel (dichloromethane:methanol, 1-15%)

出典と根拠

ORDレコード
ord-9279d1a0e83948498c2cfe39a75431e7
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08575150B2

反応ノート

読み込み中…

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