Hydrochloric Acid → HCID 57928305, compound

HRID 1360187Notes

Reaction equation

HRID 1360187 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10](C(OCC)=O)[N:9]=2)=[CH:6][N:5]=[C:4]2[NH:18][CH:19]=[CH:20][C:3]=12.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[CH:10][N:9]=2)=[CH:6][N:5]=[C:4]2[NH:18][CH:19]=[CH:20][C:3]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57928562HCID 57928562, compound

Product 1

HCID 57928305HCID 57928305, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 5-(4-chloro-1H-pyrrolo[2,3-b]pyridine-5-yl)-1,2,4-oxadiazole-3-carboxylate (350 mg) in ethanol (3.5 ml) was added 1M aqueous sodium hydroxide (1.79 ml), and the reaction solution was stirred at 50° C. for 3 hours. The reaction solution was cooled to 4° C., and 1M hydrochloric acid was added to acidify the solution. The mixture was extracted with a mixture of chloroform and methanol (4:1) and washed with water. The organic layer was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain 4-chloro-5-(1,2,4-oxadiazole-5-yl)-1H-pyrrolo[2,3-b]pyridine (215 mg) as a white solid.

Workup

  1. temperatureThe reaction solution was cooled to 4° C.
  2. extractionThe mixture was extracted with a mixture of chloroform and methanol (4:1)
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a2c8ddda29c44159c30e1c6fbf13813
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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