Water → HCID 58763660, compound

HRID 2110180Notes

Reaction equation

HRID 2110180 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14](Br)[CH:13]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33].O>O1CCOCC1.[Cu]I>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([N:28]2[CH2:32][CH2:31][CH2:30][C:29]2=[O:33])[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 58763671Methyl 2-{[(2-bromopyridin-4-yl)methyl]amino}benzoate

Product 1

HCID 58763660HCID 58763660, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

870 mg (2.78 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid methyl ester, 53 mg (0.28 mmol) of copper (I) iodide, 1.126 g (5.5 mmol) of potassium phosphate and 0.26 ml (3.6 mmol) of pyrrolidin-2-one are refluxed in 15 ml of dioxane for 8 hours. After water is added, the dioxane is distilled off in a vacuum, made alkaline with about 12% ammonia solution and shaken out several times with ethyl acetate. The collected ethyl acetate phase is washed, dried, filtered and concentrated by evaporation. As a residue, 700 mg (77% of theory) of 2-{[2-(2-oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-benzoic acid methyl ester is obtained as a crude product, which is used without further purification in the next stage.

Workup

  1. distillationthe dioxane is distilled off in a vacuum
  2. washThe collected ethyl acetate phase is washed
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-998c92eef4e443a0855c670ecf509fc6
Source dataset
uspto-grants-2009_04
Patent number
US07517894B2

Reaction notes

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