Potassium Carbonate → Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

HRID 405237Notes

Reaction equation

HRID 405237 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH:28]=[O:29])=[C:23](B(O)O)[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:28]=[O:29])=[C:21]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=2)[CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 38069525-Chloro-2-formylphenylboronic acidHCID 62959749Ethyl 3-(5-bromopicolinamido)propanoate

Product 1

HCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 3-(5-bromopicolinamido)propanoate (2.2 g, 7.3 mmol), (5-chloro-2-formylphenyl)boronic acid (1.4 g, 7.7 mmol), Pd(dppf)Cl2 (810 mg, 1.1 mmol), and K2CO3 (2.3 g, 16.9 mmol) and PdCl2(dppf) were dissolved in wet DMF (10 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, filtered through CELITE and the filtrate was diluted with EtOAc, washed with water and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. temperatureAfter 16 h the resulting mixture was cooled to room temperature
  2. filtrationfiltered through CELITE
  3. additionthe filtrate was diluted with EtOAc
  4. washwashed with water and sat. aqueous NaHCO3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-28d523e14b8342a2895a55997efc6abd
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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