Methanol → (6-chloro-2-methoxypyridin-3-yl)(1H-pyrrolo[2,3-b]pyridin-3-yl)methanol

HRID 1256726Notes

Reaction equation

HRID 1256726 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Cl:10][C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([CH:19]=[O:20])=[CH:13][CH:12]=1.CO.[OH-].[K+]>ClCCl>[Cl:10][C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([CH:19]([C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[OH:20])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 108559456-Chloro-2-methoxypyridine-3-carbaldehyde

Product 1

HCID 59593342(6-chloro-2-methoxypyridin-3-yl)(1H-pyrrolo[2,3-b]pyridin-3-yl)methanolYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1H-Pyrrolo[2,3-b]pyridine (1, 0.455 g, 3.85 mmol) and 6-chloro-2-methoxypyridine-3-carbaldehyde (26, 0.661 g, 3.85 mmol) was added methanol (10 mL) followed by potassium hydroxide (0.310 g, 5.52 mmol). The reaction was allowed to stir at room temperature overnight. The reaction was extracted with diethyl ether/ethyl acetate and water. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and volatiles were removed by rotary evaporation to provide a solid that was treated with dichloromethane and stored in a freezer overnight. The white solid was collected by vacuum filtration and dried in vacuo to give 613 mg of compound 27 (2.12 mmol, 55%). MS (ESI) [M+H+]+=290.1.

Workup

  1. extractionThe reaction was extracted with diethyl ether/ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customvolatiles were removed by rotary evaporation
  6. customto provide a solid
  7. waitstored in a freezer overnight
  8. filtrationThe white solid was collected by vacuum filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-4c5a24d774aa43caa40ff714d9cb7f82
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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