Potassium Hydroxide → 3-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1820877

Reaction equation

HRID 1820877 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]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:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:10][CH:11]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 578917891-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

1-Benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (5, 290 mg, 0.74 mmol) was dissolved in ethanol (4 mL) and potassium hydroxide pellets (330 mg, 5.9 mmol) were added. The reaction 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 portions were dried with anhydrous magnesium sulfate, filtered and the filtrate concentrated to provide the desired product, 1, which was used without further purification (191 mg). MS(ESI) [M+H+]+=255.1.

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 portions were dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-179b2ddb05eb4277bc60b00d6e05fe0e
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Linked notes

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