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

HRID 405213Notes

Reaction equation

HRID 405213 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([CH:30]=[O:31])=[C:25](B(O)O)[CH:26]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O.O.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:20][C:21]1[CH:26]=[CH:25][C:24]([CH:30]=[O:31])=[C:23]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=2)[CH:22]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 38069525-Chloro-2-formylphenylboronic acidHCID 71060050Tert-butyl 3-(5-bromopicolinamido)propanoate

Product 1

HCID 86674275Tert-butyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 3-(5-bromopicolinamido)propanoate (3.4 g, 10.3 mmol), (5-chloro-2-formylphenyl)boronic acid (2.1 g, 11.3 mmol), Pd(dppf)Cl2 (840 mg, 1.0 mmol), and K2CO3 (3.1 g, 22.6 mmol) were dissolved in 1,4-dioxane (35 mL) and water (9 mL) and heated to 90° C. After 3 h the resulting mixture was cooled to room temperature, diluted with EtOAc and water and the layers were separated. The combined organics were washed dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. customthe layers were separated
  2. washThe combined organics were washed
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-f9f8be8d853f46428403aa5ec5604dff
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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