Water → Ethyl 3-(5-(4-chloro-2-formylphenyl)picolinamido)propanoate

HRID 405117Notes

Reaction equation

HRID 405117 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:24]=[CH:23][C:22](B(O)O)=[C:21]([CH:28]=[O:29])[CH:20]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=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:18][C:19]1[CH:24]=[CH:23][C:22]([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)=[C:21]([CH:28]=[O:29])[CH:20]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 237304254-Chloro-2-formylphenylboronic Acid (contains varying amounts of Anhydride)HCID 62959749Ethyl 3-(5-bromopicolinamido)propanoate

Product 1

HCID 86674245Ethyl 3-(5-(4-chloro-2-formylphenyl)picolinamido)propanoate

Reagents, catalysts & solvents 3

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

Procedure

Ethyl 3-(5-bromopicolinamido)propanoate, prepared as in Example 1, (1.5 g, 5.0 mmol), (4-chloro-2-formylphenyl)boronic acid (1.0 g, 5.5 mmol), Pd(dppf)Cl2 (408 mg, 0.5 mmol), and K2CO3 (1.4 g, 10.0 mmol) were dissolved in 1,4-dioxane (20 mL) and water (5 mL) and heated to 80° C. After 3 h the resulting mixture was cooled to room temperature, diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry-packed onto silica gel and purified via column chromatography

Sources & evidence

ORD record
ord-2cf8dfad81df45efb15a06da29f771b7
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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