HCID 69526653, compound → HCID 22054885, compound

HRID 1829808Notes

Reaction equation

HRID 1829808 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:12]2)C1C=CC=CC=1>CCO.C1COCC1.[Pd]>[CH3:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[C:13]1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 1

HCID 69526653HCID 69526653, compound

Product 1

HCID 22054885HCID 22054885, compoundYield 72.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(benzyloxy)-1-methyl-2-(2-phenylethenyl)-1H-indole (204 mg, 0.601 mmol) in EtOH (5 ml) and THF (5 ml) was added 10% palladium on carbon (50 mg). The resulting mixture was stirred under hydrogen (2 atm) for 15 h at room temperature. The mixture was filtered through Celite and washed with EtOH. The filtrate was concentrated in vacuo and then the residue was purified by silica gel (4.5 g) chromatography eluted with chloroform to give 1-methyl-2-(2-phenylethyl)-1H-indol-5-ol (110 mg, 72.8%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel (4.5 g) chromatography
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-0a012d46e39e4f4d99ccc19ae399f3ef
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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