Potassium Hydroxide → 3-(2,6-Dichloro-4-pyridinyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 2089018

Reaction equation

HRID 2089018 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[CH:9]=2)[CH:5]=[C:4]([Cl:28])[N:3]=1.[OH-].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[C:4]([Cl:28])[N:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 871925543-(2,6-dichloropyridin-4-yl)-5-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 871921833-(2,6-Dichloro-4-pyridinyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridineYield 85.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of Example 149d (88.0 mg, 0.203 mmol) in ethanol (2 mL) was treated with a solution of potassium hydroxide (45.5 mg, 0.811 mmol) in water (0.5 mL). The reaction mixture was heated at 50° C. for 1.5 hours. After concentration, water was added to the residue and the mixture was sonicated. The solid was filtered, washed with water, and oven-dried to give 51.3 mg of the title compound.

Workup

  1. concentrationAfter concentration, water
  2. additionwas added to the residue
  3. customthe mixture was sonicated
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customoven-dried

Sources & evidence

ORD record
ord-e69bb49baf794e34b733545ae9b2740b
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Linked notes

Loading…