1-(3-Fluoro-4-pyridinylamino)-5-phenylmethoxy-1H-indole → 1-(3-Fluoro-4-pyridinylamino)-1H-indol-5-ol

HRID 1029726Notes

Reaction equation

HRID 1029726 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18]CC3C=CC=CC=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

5

Reactant 2

HCID 199004641-(3-Fluoro-4-pyridinylamino)-5-phenylmethoxy-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 199004851-(3-Fluoro-4-pyridinylamino)-1H-indol-5-olYield 137.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

In a 500 ml Parr hydrogenation bottle, 10% Pd/C (1.0 g) was suspended in 50 ml ethanol, and to this was added a solution of 1-(3-fluoro-4-pyridinylamino)-5-phenylmethoxy-1H-indole (5.0 g) in 200 ml ethanol. The mixture was shaken at 50° C. under 50 psi hydrogen gas for two hours. After cooling, the mixture was filtered, and the filtrate was concentrated to give an oil (5.0 g) which was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC. The desired fractions were combined and concentrated to give a crystalline solid, 3.5 g, m.p. 70°-73° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-21665ff9206c436493bf5880b3acc1c8
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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