HCID 19900463, compound → HCID 19900479, compound

HRID 1029712Notes

Reaction equation

HRID 1029712 reaction equation
[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[N:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12]CC3C=CC=CC=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4]1>C(O)C>[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[N:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

3

Reactant 1

HCID 19900463HCID 19900463, compound

Product 1

HCID 19900479HCID 19900479, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(methyl-4-pyridinylamino)-5-phenylmethoxy-1H-indole (9 g) in 250 mL ethanol containing 0.6 g 10% palladium on activated charcoal was hydrogenated at 50 psi at 50° C. for three hours via Parr hydrogenation apparatus. After cooling, the mixture was filtered through Celite and concentrated. The residue was eluted through silica with 5% methanol in dichloromethane via flash column chromatography to yield 6.2 g solid. A three gram portion was recrystallized from acetonitrile to yield 2.6 g solid, m.p. 191°-193° C. This was again recrystallized from acetonitrile to yield 2.2 g crystals, m.p. 192°-193° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through Celite
  3. concentrationconcentrated
  4. washThe residue was eluted through silica with 5% methanol in dichloromethane via flash column chromatography

Sources & evidence

ORD record
ord-54fce87a56444d7ca6bc7786196d258e
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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