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4-fluoro-2-methyl-1H-indol-5-ol → 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline

HRID 1510102
ノート
印刷プレビュー

反応式

HRID 1510102 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:22][C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[C:29]([F:32])[C:28]([OH:33])=[CH:27][CH:26]=2>CN(C1C=CN=CC=1)C.O1CCOCC1.CCOC(C)=O.O>[F:32][C:29]1[C:28]([O:33][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:27][CH:26]=[C:25]2[C:30]=1[CH:31]=[C:23]([CH3:22])[NH:24]2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

生成物 1

HCID 592007474-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒
HCID 8857
Ethyl Acetate
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

4-Chloro-7-benzyloxy-6-methoxy-quinoline (WO2008112407, 1.5 g) was mixed with DMAP (1.5 eq), 2-methyl-4-fluoro-5-hydroxyindole (WO0047212) (1 eq) in dioxane (20 ml). The reaction was refluxed for three days and diluted with EtOAc, water and extracted with EtOAc three times. The combined organic layer was washed with water, brine and dried. The solution was evaporated and purified with silica gel column to give 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline (600 mg).

後処理

  1. temperatureThe reaction was refluxed for three days
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layer was washed with water, brine
  4. customdried
  5. customThe solution was evaporated
  6. custompurified with silica gel column

出典と根拠

ORDレコード
ord-19f0907e8cdb45f69fa35c78336f2dcb
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08211911B2

反応ノート

読み込み中…

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