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

HRID 25529Notes

Reaction equation

HRID 25529 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.[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][CH2:5][C:4]3[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([OH:1])[CH:3]=3)[CH:29]=1)=[CH:17]2

Participants

7

Reactant 4

HCID 697123-Hydroxy-4-nitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

Product 1

HCID 10226571[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-(3-hydroxy-4-nitro-benzyl)-amineYield 41.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-4-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 (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 3 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-orange gum. Recrystallization from methanol gave the product (350 mg), mp 170-171° C.

Workup

  1. stirringthe resulting homogeneous solution was stirred at room temperature for 3 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-orange gum
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-b794240a450847f7b2bbcba41b93927f
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

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