Methanol → HCID 86672870, compound

HRID 2403698Notes

Reaction equation

HRID 2403698 reaction equation
[C:1]([C:3]1[NH:16][C:6]2=[N:7][CH:8]=[C:9]([C:11]([O:13]CC)=[O:12])[CH:10]=[C:5]2[CH:4]=1)#[N:2].CO.O1CCCC1.[OH-].[Li+]>O>[C:1]([C:3]1[NH:16][C:6]2=[N:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=[C:5]2[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 70896196HCID 70896196, compound

Product 1

HCID 86672870HCID 86672870, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 2-cyano-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (36 mg, 0.17 mmol) was added methanol (1 mL), tetrahydrofuran (1 mL), and water (1 mL), followed by 2 N aqueous lithium hydroxide (0.17 mL, 0.33 mmol). The reaction was stirred at room temperature overnight and was then concentrated. The crude was taken up in water and the pH was adjusted to 4 using 1 N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate (3×). The combined organics were dried over sodium sulfate, filtered, and concentrated to provide the 2-cyano-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid. The title compound was then prepared by a method analogous to that described in Example 1, using 2-cyano-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid. −ESI (M−H) 415.1.

Workup

  1. concentrationwas then concentrated
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff686adb9604458b98f8ce7a7718a82c
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

Loading…