Potassium Phosphate, Tribasic → 1-(5-Chloropyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester

HRID 1748484Notes

Reaction equation

HRID 1748484 reaction equation
CN(C)CCN.[C:7]([O:11][C:12]([C:14]1[CH:18]=[CH:17][NH:16][CH:15]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1>O1CCOCC1.[Cu](I)I.O>[C:7]([O:11][C:12]([C:14]1[CH:18]=[CH:17][N:16]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=2)[CH:15]=1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66053N,N-DimethylethylenediamineHCID 8170982-Bromo-5-chloropyridineHCID 11171190tert-butyl 1H-pyrrole-3-carboxylate

Product 1

HCID 866924471-(5-Chloropyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl esterYield 90%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

N,N-dimethylethylenediamine (1.9 ml) was added to 1H-pyrrole-3-carboxylic acid tert-butyl ester (2.0 g) described in Reference Example 50, copper iodide (2.28 g), tripotassium phosphate (12.7 g) and 2-bromo-5-chloropyridine (2.78 g) in 1,4-dioxane (120 ml), and stirred at 120° C. for four hours. Water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated in vacuo. n-Hexane was added to the resulting residue and the precipitated solid was washed with n-hexane to give 1-(5-chloropyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester (3.0 g) as a gray solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionn-Hexane was added to the resulting residue
  5. washthe precipitated solid was washed with n-hexane

Sources & evidence

ORD record
ord-6b00bd18cc544d2088dd4f2625b5be44
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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