Methanol → 3-Amino-7-fluoro-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264931Notes

Reaction equation

HRID 2264931 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:9]=1[NH:10][CH3:11])[C:7]#[N:8].[H-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].CO>CN(C=O)C>[CH2:19]([O:18][C:16]([C:15]1[N:10]([CH3:11])[C:9]2[C:2]([F:1])=[CH:3][N:4]=[CH:5][C:6]=2[C:7]=1[NH2:8])=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 595965925-Fluoro-4-methylamino-nicotinonitrile

Product 1

HCID 595966593-Amino-7-fluoro-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Fluoro-4-methylamino-nicotinonitrile (2.35 g, 15 mmol) was dissolved in DMF (50 mL) and the solution cooled in an ice-bath. This solution was treated portionwise with sodium hydride (900 mg, 60% in oil, 22.5 mmol). The mixture was allowed to warm to room temperature and stirring continued for 15 minutes at room temperature. Ethyl bromoacetate (2.49 ml, 22.5 mmol) was added and the mixture stirred for 30 minutes at room temperature The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was isolated, dried (Na2SO4) and evaporated to give a solid. Trituration of the resultant solid with methanol gave the title compound (1.85 g, 52%) as a yellow solid. LCMS (method B): RT=2.09 min, M+H+ 238.

Workup

  1. temperaturethe solution cooled in an ice-bath
  2. stirringthe mixture stirred for 30 minutes at room temperature The reaction mixture
  3. customwas quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was isolated
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a solid

Sources & evidence

ORD record
ord-2f9613e9d6f0436fbca8b130647db14f
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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