HCID 18679567, compound → HCID 18679499, compound

HRID 1633652Notes

Reaction equation

HRID 1633652 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1)[CH:13]=[CH:12]2)C1C=CC=CC=1>CCOC(C)=O.CCO.CCCCCC.CCOC(C)=O.[Pd]>[C:18]1([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:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 1

HCID 18679567HCID 18679567, compound

Product 1

HCID 18679499HCID 18679499, compoundYield 62.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

3.8 g (10 mmol) 5-Benzyloxy-1-(4-bromo-phenyl)-1H-indole in 30 ml EtOAc and 10 ml EtOH were hydrogenated in the presence of 5% Pd/C. Column chromatography on silica gel in hexane/EtOAc 5:1 yielded 1.3 g (62%) 1-Phenyl-1H-indol-5-ol as colorless viscous oil, MS: 209 (M).

Sources & evidence

ORD record
ord-5e67c18e47c1468584f30138cf4a261a
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

Loading…