HCID 70147593, compound → HCID 70146441, compound

HRID 1955676Notes

Reaction equation

HRID 1955676 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>[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

3

Reactant 1

HCID 70147593HCID 70147593, compound

Product 1

HCID 70146441HCID 70146441, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[(3-Fluoro-4-pyridinyl)propylamino]-3-methyl-5-(phenylmethoxy)-1H-indole (15.8 g) was dissolved in absolute ethanol (200 ml) and hydrogenated at 344.74 Kpa (Parr shaker, 50 psi) at 50° C. for seven and one-half hours. Thereafter, the mixture was filtered and the solids were washed with absolute ethanol. The combined filtrates were concentrated and the residue was purified via preparative HPLC (silica, 3:1 dichloromethane/ethyl acetate) to afford an oil (5.0 g) Addition of ethyl acetate solidified the product which was recrystallized from ethyl acetate to give a solid, m.p. 157°-160° C.

Workup

  1. filtrationThereafter, the mixture was filtered
  2. washthe solids were washed with absolute ethanol
  3. concentrationThe combined filtrates were concentrated
  4. customthe residue was purified via preparative HPLC (silica, 3:1 dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-d9ecb5f3861d4ebd887fb2cae9a87047
Source dataset
uspto-grants-1998_07
Patent number
US05776955

Reaction notes

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