Lithium Hydroxide → HCID 90027529, compound

HRID 2275000Notes

Reaction equation

HRID 2275000 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:6]2[CH:5]=[C:4]1[C:14]([O:16]CC)=[O:15])[CH3:2].[OH-].[Li+]>C1COCC1.CO.O>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:6]2[CH:5]=[C:4]1[C:14]([OH:16])=[O:15])[CH3:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 90033749HCID 90033749, compound

Product 1

HCID 90027529HCID 90027529, compoundYield 60.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-ethyl-5-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (60 mg, 0.24 mmol) in THF (2 ml) and MeOH (0.5 ml) was added lithium hydroxide (35 mg, 1.45 mmol) in water (2 mL). A cloudy solution formed which became clear after 30 s. The reaction mixture was allowed to stand at room temperature for 18 hr then concentrated under a stream of nitrogen. 2M HCl (2 ml, aqueous) was added to the crude product and the resulting solid filtered then dried under reduced pressure to give the title compound as an off-white solid (32 mg, 60%).

Workup

  1. customA cloudy solution formed which
  2. waitto stand at room temperature for 18 hr
  3. concentrationthen concentrated under a stream of nitrogen
  4. addition2M HCl (2 ml, aqueous) was added to the crude product
  5. filtrationthe resulting solid filtered
  6. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-23fc7b18c82e4b3ab71aacd0fd1f8ce1
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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