Water → HCID 86674276, compound

HRID 405224Notes

Reaction equation

HRID 405224 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:9])=[N:6][CH:7]=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH:27]=[O:28])=[C:22](B(O)O)[CH:23]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.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].CCOC(C)=O.O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:27]=[O:28])=[C:20]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:9])=[N:6][CH:7]=2)[CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 38069525-Chloro-2-formylphenylboronic acidHCID 62958519HCID 62958519, compound

Product 1

HCID 86674276HCID 86674276, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

Methyl 3-(5-bromopicolinamido)propanoate (2.0 g, 7.0 mmol), (5-chloro-2-formylphenyl)boronic acid (1.4 g, 7.7 mmol), Pd(dppf)Cl2 (572 mg, 0.7 mmol), and K2CO3 (2.1 g, 15.4 mmol) were dissolved in 1,4-dioxane (24 mL) and water (6 mL) and heated to 90° C. After 3 h the resulting mixture was poured into EtOAc/H2O (30 mL/30 mL) and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic layers were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-8ef9df2081754ee0b442ac496bed4b60
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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