4-Nitrobenzaldehyde → [5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-4nitro-benzylamine

HRID 25528

反応式

HRID 25528 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[F:22])[NH:18][C:17]([C:23]1[CH:24]=[CH:25][C:26]([O:30][CH3:31])=[C:27]([NH2:29])[CH:28]=1)=[CH:16]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:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[F:22])[NH:18][C:17]([C:23]1[CH:24]=[CH:25][C:26]([O:30][CH3:31])=[C:27]([NH:29][CH2:8][C:7]3[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH:28]=1)=[CH:16]2

参加物

7

反応物 4

HCID 5414-NitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

生成物 1

HCID 10272905[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-4nitro-benzylamine収率 55%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Nitrobenzaldehyde (0.3 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 (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 6 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added, and the mixture was stirred for 2 hours. The mixture was shaken; the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give a red solid. Recrystallization from methanol gave the product (450 mg), mp 181-182° C.

後処理

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

出典と根拠

ORDレコード
ord-e5680f1e35684a7e8e714f326cfd5c99
出典データセット
uspto-grants-2005_02
特許番号
US06858739B2

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