Acetic Acid → [5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-(4-methoxy-benzyl)-amine

HRID 25502

Reaktionsgleichung

Reaktionsgleichung von HRID 25502
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[F:21])[NH:17][C:16]([C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH2:28])[CH:27]=1)=[CH:15]2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[F:21])[NH:17][C:16]([C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH:28][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:27]=1)=[CH:15]2

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

Produkt 1

HCID 10294027[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-(4-methoxy-benzyl)-amineAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Methoxybenzaldehyde (0.204 g, 1.5 mmol) was added to a stirred mixture of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (0.405 g, 1.48 mmol) in methylene chloride (125 mL), followed by acetic acid (0.3 g, 1.5 mmol). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.31 g, 1.46 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 3 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 a yellow oil. Recrystallization from methanol/water gave the product as off-white crystals (270 mg); mp 173-175° C.

Aufarbeitung

  1. stirringthe resulting homogeneous solution stirred at room temperature for 3 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 a yellow oil
  8. customRecrystallization from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-5446955f4f5346a18a8e2ea598f19e1b
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858739B2

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