5-Phenylmethoxy-1-(4-pyridinylamino)-1H-indole → HCID 19900488, compound

HRID 1029711Notes

Reaction equation

HRID 1029711 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:13]=[CH:12]3)C=CC=CC=1>[Pd].C(O)C>[N:22]1[CH:23]=[CH:24][C:19]([NH:18][N:14]2[C:15]3[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 149882825-Phenylmethoxy-1-(4-pyridinylamino)-1H-indole

Product 1

HCID 19900488HCID 19900488, compoundYield 147%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To 0.8 g of 10% palladium on carbon in 10 ml of absolute ethanol was added a solution of 5-(phenylmethoxy)-1-(4-pyridinylamino)-1H-indole (4.0 g) in 240 ml of absolute ethanol and this was hydrogenated on a Parr apparatus for four hours at 50° C. at 50 psig H2. The mixture was cooled and filtered, and the filtrate was concentrated to yield an oil (4.2 g), which was eluted with ethyl acetate on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil (3.72 g). This material was eluted with 10% methanol/dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield a foam (1.8 g), which was recrystallized from ethyl acetate to yield a solid (1.5 g), m.p. 232°-234° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-429399a35409478e8d83c5338994dc44
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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