Potassium Hydroxide → 3-(3,4-Dimethoxyphenyl)-1H-indole

HRID 1820881Notes

Reaction equation

HRID 1820881 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[K+]>C(O)C>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][CH:11]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 578917491-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-indole

Product 1

HCID 447206813-(3,4-Dimethoxyphenyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

1-Benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-indole (350 mg, 0.89 mmol) 19 was dissolved in ethanol (3 mL) and potassium hydroxide pellets (385 mg, 6.9 mmol) were added. The reaction mixture was heated in a CEM Discover microwave instrument at 120° C. for 10 minutes. The reaction mixture was concentrated to dryness and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic portion was dried with anhydrous magnesium sulfate, filtered and the filtrate concentrated to provide the desired product 22, which was used without further purification (208 mg, 92%)

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. dry with materialThe organic portion was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-8682156b8a924a44bc8057e4ae568c47
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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