HCID 14988293, compound → HCID 18960815, compound

HRID 1029715Notes

Reaction equation

HRID 1029715 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([N:18]([CH2:25][CH2:26][CH3:27])[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:13]=[CH:12]3)C=CC=CC=1>C(O)C.[Pd]>[CH2:25]([N:18]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)[CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 14988293HCID 14988293, compound

Product 1

HCID 18960815HCID 18960815, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To 0.3 g of 10% Pd/C in 10 ml of absolute ethanol was added 5-phenylmethoxy-1-(propyl-4-pyridinylamino)-1H-indole (3.0 g) in 240 ml of ethanol and this was hydrogenated on a Parr apparatus for 48 hours at 50° C. and 50 psig H2. The reaction mixture was then filtered and the filtrate concentrated to yield an oil (2.2 g), which was eluted with 5% methanol/dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield a solid (1.8 g) which was recrystallized from methanol/ether (1:1) to yield a solid 1.6 g, m.p. 214°-216° C.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-a15369bfc5c44f249f511cdd46b7b679
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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