Dimethylformamide → HCID 58778584、化合物

HRID 1372712

反応式

HRID 1372712 の反応式
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:12]([OH:14])=O)=[CH:5][N:6]2[CH3:11].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:26][C:27]1[C:32]([Cl:33])=[CH:31][C:30]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:29]([F:40])[CH:28]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:33][C:32]1[C:27]([NH:26][C:12]([C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])[N:6]([CH3:11])[CH:5]=2)=[O:14])=[CH:28][C:29]([F:40])=[C:30]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:31]=1

参加物

8

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chloride2 回HCID 17858807Ethyl 4-amino-5-chloro-2-fluorophenylacetateHCID 183852904-Fluoro-1-methyl-1h-indole-3-carboxylic acid

生成物 1

HCID 58778584HCID 58778584、化合物収率 52%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 4-fluoro-1-methylindole-3-carboxylic acid (700 mg, 3.62 mmol) and DMF (28.0 μl, 0.36 mmol) in methylene chloride (20 ml) was added oxalyl chloride (0.35 ml, 3.99 mmol) in portions under stirring at room temperature. After the reaction mixture was stirred at room temperature for 50 minutes, oxalyl chloride (30 μl) was added, and the mixture was stirred for further 40 minutes. To the reaction mixture, a solution of ethyl (4-amino-5-chloro-2-fluorophenyl)acetate (839 mg, 3.62 mmol) and triethylamine (1.52 ml, 10.9 mmol) in methylene chloride (5 ml) was added and the mixture was heated under reflux at room temperature for 4 hours. After cooling to room temperature, the reaction mixture was added with water, followed by extraction with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography opn a silica gel column, whereby from n-hexane-ethyl acetate (2:1, v/v) eluate fractions, ethyl (5-chloro-2-fluoro-4-((4-fluoro-1-methyl-3-indolylcarbonyl)amino)phenyl)acetate (762 mg, 52%) was obtained as a yellow solid.

後処理

  1. stirringAfter the reaction mixture was stirred at room temperature for 50 minutes
  2. stirringthe mixture was stirred for further 40 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux at room temperature for 4 hours
  5. temperatureAfter cooling to room temperature
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by chromatography opn a silica gel column, whereby from n-hexane-ethyl acetate (2:1

出典と根拠

ORDレコード
ord-9ef4e488fa0941d596f58d7f864149ad
出典データセット
uspto-grants-2007_01
特許番号
US07157487B2

関連ノート

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