Water → Ethyl 3-(5-(2-formyl-5-methoxyphenyl)picolinamido)propanoate

HRID 405164Notes

Reaction equation

HRID 405164 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.[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1B(O)O)=[O:19].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]>[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[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)=[O:19]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343665-Methoxy-2-formylphenylboronic acidHCID 62959749Ethyl 3-(5-bromopicolinamido)propanoate

Product 1

HCID 86674253Ethyl 3-(5-(2-formyl-5-methoxyphenyl)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 (1.0 g, 3.3 mmol), (2-formyl-5-methoxyphenyl)boronic acid (777 mg, 4.3 mmol), Pd(dppf)Cl2 (364 mg, 0.5 mmol), and K2CO3 (918 mg, 6.6 mmol) were dissolved in 1,4-dioxane (20 mL) and water (5 mL) and heated to 80° C. After 2 h the resulting mixture was cooled to room temperature, diluted with EtOAc washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-19d6fa426416489095ad6f9e9c7a1a8b
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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