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Dimethylformamide → 4-(4-Amino-3-fluoro-phenoxy)-7-[(2R)-oxiran-2-yl]methoxyquinoline-6-carbonitrile

HRID 1433613
ノート
印刷プレビュー

反応式

HRID 1433613 の反応式
CN(C)C=O.CC1C=CC(S(O[CH2:17][C@@H:18]2[O:20][CH2:19]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[NH2:27][C:28]1[CH:47]=[CH:46][C:31]([O:32][C:33]2[C:42]3[C:37](=[CH:38][C:39]([OH:45])=[C:40]([C:43]#[N:44])[CH:41]=3)[N:36]=[CH:35][CH:34]=2)=[CH:30][C:29]=1[F:48]>C(OCC)(=O)C.O>[NH2:27][C:28]1[CH:47]=[CH:46][C:31]([O:32][C:33]2[C:42]3[C:37](=[CH:38][C:39]([O:45][CH2:17][C@H:18]4[CH2:19][O:20]4)=[C:40]([C:43]#[N:44])[CH:41]=3)[N:36]=[CH:35][CH:34]=2)=[CH:30][C:29]=1[F:48]
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

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 1358293794-(4-Amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline

生成物 1

HCID 865914714-(4-Amino-3-fluoro-phenoxy)-7-[(2R)-oxiran-2-yl]methoxyquinoline-6-carbonitrile収率 55.4%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

After adding dimethylformamide (8 ml), (2R)-(−)-glycidyl p-toluenesulfonate (1000 mg) and potassium carbonate (940 mg) to 4-(4-amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline (1000 mg), the mixture was heated at 50° C. for 4 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (659 mg) as light yellow crystals.

後処理

  1. washthe organic layer was washed with water and saturated brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-f2aabb7218e2453b9fb1892a29762e8c
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612092B2

反応ノート

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