4-Hydroxy-3-nitrobenzaldehyde → [5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl](4-hydroxy-3-nitro-benzyl)-amine

HRID 25530

反応式

HRID 25530 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[F:23])[NH:19][C:18]([C:24]1[CH:25]=[CH:26][C:27]([O:31][CH3:32])=[C:28]([NH2:30])[CH:29]=1)=[CH:17]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[F:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[F:23])[NH:19][C:18]([C:24]1[CH:25]=[CH:26][C:27]([O:31][CH3:32])=[C:28]([NH:30][CH2:6][C:5]3[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=3)[CH:29]=1)=[CH:17]2

参加物

7

反応物 4

HCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

生成物 1

HCID 10180739[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl](4-hydroxy-3-nitro-benzyl)-amine収率 35.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Hydroxy-3-nitrobenzaldehyde (0.334 g, 2.0 mmol) was added to a stirred mixture of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (0.548 g, 2.0 mmol) in methylene chloride (125 mL), followed by acetic acid (0.2 g). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.47 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 7 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture stirred for 2 hours. The mixture was shaken, the organic layer separated and dried over Na2SO4. The solvent was evaporated to give an orange solid. Recrystallization from methanol gave the product (300 mg), mp 195-196° C.

後処理

  1. stirringthe resulting homogeneous solution stirred at room temperature for 7 days
  2. stirringthe mixture stirred for 2 hours
  3. stirringThe mixture was shaken
  4. customthe organic layer separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customto give an orange solid
  8. customRecrystallization from methanol

出典と根拠

ORDレコード
ord-1fcdb3f9e6bb4172889cf75f84c01c6f
出典データセット
uspto-grants-2005_02
特許番号
US06858739B2

関連ノート

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