Water → Tert-butyl 3-(5-(2-formylphenyl)picolinamido)propanoate

HRID 405113Notes

Reaction equation

HRID 405113 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.[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O)=[O:21].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:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[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)=[O:21]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2921892-Formylphenylboronic acidHCID 71060050Tert-butyl 3-(5-bromopicolinamido)propanoate

Product 1

HCID 86674244Tert-butyl 3-(5-(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

tert-Butyl 3-(5-bromopicolinamido)propanoate (1.0 g, 3.0 mmol), 2-formylphenylboronic acid (547 mg, 3.6 mmol), Pd(dppf)Cl2 (249 mg, 0.3 mmol), and K2CO3 (840 mg, 6.1 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-2585618b19ce4b5d968c09cec26e6ecd
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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