Methanol → 4-Methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 1020905Notes

Reaction equation

HRID 1020905 reaction equation
[OH-:1].[Na+].Cl[C:4]1[CH:12]=[CH:11][N:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH3:13]O>>[CH3:13][O:1][C:4]1[CH:12]=[CH:11][N:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 112405674-Methoxy-1H-pyrrolo[2,3-b]pyridine

Procedure

A solution of sodium hydroxide (11 g) in methanol (250 mL) was stirred with 4-chloro-1H-pyrrolo[2,3-b]pyridine (step 2)(12.2 g, 80 mmol) at 140° C. in a sealed reactor for 16 hr. After being cooled to ambient temperature the mixture was concentrated and residue was slurred in water (100 mL) for one hour. The solid was collected by suction filtration and washed to neutrality with water. After being dried to constant weight, 6.5 g of 4-methoxy-7-azaindole was obtained as a tan solid; MS (m/z) 149 (M+H).

Workup

  1. concentrationwas concentrated
  2. filtrationThe solid was collected by suction filtration
  3. washwashed
  4. customAfter being dried to constant weight

Sources & evidence

ORD record
ord-6d758ae00c394184803892307e5fcb4f
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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