m-Chloroperbenzoic acid → [3-Hydroxy-5-(1H-indol-4-YL)-phenyl]-(6-hydroxymethyl-pyridin-3-YL)-methanone

HRID 1784820Notes

Reaction equation

HRID 1784820 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:21]CC2C=CC(OC)=CC=2)[CH:20]=1)[C:5]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][O:14]C(=O)C)=[N:11][CH:12]=1)=[O:6].[CH3:31][C:32]1[N:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][CH:33]=1.[CH:40]1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[OH:21][C:19]1[CH:18]=[C:4]([C:5]([C:7]2[CH:12]=[N:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)=[O:6])[CH:3]=[C:2]([C:34]2[CH:33]=[CH:32][CH:31]=[C:36]3[C:35]=2[CH:38]=[CH:40][NH:37]3)[CH:20]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 101925666-Methyl-3-pyridinecarboxaldehydeHCID 68844896Acetic acid 5-[3-bromo-5-(4-methoxy-benzyloxy)-benzoyl]-pyridin-2-ylmethyl ester

Product 1

HCID 15604424[3-Hydroxy-5-(1H-indol-4-YL)-phenyl]-(6-hydroxymethyl-pyridin-3-YL)-methanoneYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetic acid 5-[3-bromo-5-(4-methoxy-benzyloxy)-benzoyl]-pyridin-2-ylmethyl ester. To a stirred solution of 3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-(6-methyl-pyridin-3-yl)-methanone (388 mg, 0.94 mmol) in dry methylene chloride (20 mL) at 0° C. was added dropwise a solution of MCPBA (0.371 mg, 1.50 mmol) in methylene chloride (10 mL). The resulting solution was stirred overnight. TLC indicated that the completion of the reaction. The organic phase was washed with sat. NaHCO3, dried, and concentrated. The crude product was then dissolved in Ac2O (2 mL) and the resulting solution was stirred at 150° C. for 30 min. TLC indicated that the completion of the reaction. The reaction mixture was then poured into an ice cold sat. NaHCO3 solution and stirred for 20 min. The aqueous phase was the extracted with EtOAc for three times. After removal of the solvents, the crude product was purified by flash chromatography (4:1 Hexane/EtOAc) to afford the titled product (0.140 mg, 31% over two steps).

Workup

  1. customTLC indicated that the completion of the reaction
  2. washThe organic phase was washed with sat. NaHCO3
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe crude product was then dissolved in Ac2O (2 mL)
  6. stirringthe resulting solution was stirred at 150° C. for 30 min
  7. customTLC indicated that the completion of the reaction
  8. stirringstirred for 20 min
  9. extractionextracted with EtOAc for three times
  10. customAfter removal of the solvents
  11. customthe crude product was purified by flash chromatography (4:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-7737219f4cf3499a853cb7b39ec051ff
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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