HCID 70147593, compound → HCID 70146441, compound

HRID 1029737Notes

Reaction equation

HRID 1029737 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][NH:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21]CC3C=CC=CC=3)=[CH:18][CH:19]=2)[C:14]([CH3:29])=[CH:13]1>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][NH:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=2)[C:14]([CH3:29])=[CH:13]1

Participants

4

Reactant 1

HCID 70147593HCID 70147593, compound

Product 1

HCID 70146441HCID 70146441, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The benzyl group of 1-[(3-fluoro-4-pyridinyl)propylamino]-3-methyl-5-(phenylmethoxy)-1H-indole (15.82 g) was cleaved in a Parr hydrogenation apparatus in absolute ethanol (200 ml) over 10% Pd-C (1.58 g) at 50 psig and 50° C. for 7.5 hours. The catalyst was removed by filtration through a pad of celite and the solids washed with absolute ethanol. The combined filtrate was concentrated and the product purified via preparative HPLC (silica gel, 3:1 dichloromethane/EtOAc) affording 5.0 g of the desired product as an oil. Addition of EtOAc solidified the product which was recrystallized from EtOAc to give a solid, m.p. 157°-160° C.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. washthe solids washed with absolute ethanol
  3. concentrationThe combined filtrate was concentrated
  4. customthe product purified via preparative HPLC (silica gel, 3:1 dichloromethane/EtOAc)

Sources & evidence

ORD record
ord-2d818ae3965047c99780f4e2abbc8b17
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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