Carbon Dioxide → 1H-pyrrolo[2,3-b]pyridin-4-ol

HRID 549087Notes

Reaction equation

HRID 549087 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[OH-].[Na+].C(=O)=[O:14]>>[NH:8]1[C:4]2[N:5]=[CH:6][CH:7]=[C:2]([OH:14])[C:3]=2[CH:10]=[CH:9]1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 14798Sodium Hydroxide2×HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 1785164671H-pyrrolo[2,3-b]pyridin-4-ol

Conditions

Temperature
180 °C

Procedure

4-Chloro-1H-pyrrolo-[2,3-b]pyridine [80 g, Reference Example 64] was treated with 10% aqueous sodium hydroxide solution (330 g) and heated to 180° C. for 8 hours in a parr bomb with magnetic stirring. The reaction mixture was cooled to room temperature and excess sodium hydroxide was neutralized with a large excess of solid carbon dioxide pellets. Undissolved starting material was removed by filtration and the filtrate was concentrated in vacuo. The residue was extracted with hot methanol (3×1000 mL). The combined methanol extracts were concentrated and the residue purified by flash column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (9:1 v:v to 4:1 v:v) to afford the title compound as a solid (63 g). TLC: RF=0.32 (dichloromethane/methanol 4/1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. extractionThe residue was extracted with hot methanol (3×1000 mL)
  5. concentrationThe combined methanol extracts were concentrated
  6. customthe residue purified by flash column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (9:1 v:v to 4:1 v:v)

Sources & evidence

ORD record
ord-cb2ac7a5db4e4383bd7ab2df263b3d72
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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