Potassium Carbonate → HCID 117696310, compound

HRID 2205283Notes

Reaction equation

HRID 2205283 reaction equation
CB1OB(C)OB(C)O1.[C:10]([NH:14][C:15]([C:17]1[C:22]([CH2:23][C:24](=[O:26])[CH3:25])=[C:21](Cl)[CH:20]=[CH:19][N:18]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:28](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:10]([NH:14][C:15]([C:17]1[C:22]([CH2:23][C:24](=[O:26])[CH3:25])=[C:21]([CH3:28])[CH:20]=[CH:19][N:18]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 117696450HCID 117696450, compound

Product 1

HCID 117696310HCID 117696310, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Trimethylboroxine (5.7 mL, 41 mmol) is added to 4-chloro-3-(2-oxo-propyl)-pyridine-2-carboxylic acid tert-butylamide (3.63 g, 13.5 mmol), potassium carbonate (9.33 g, 67.5 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(11)dichloride dichloromethane complex (1.10 g, 1.35 mmol) in DMF (60 mL) and the reaction mixture is heated at 100° C. overnight. Volatiles are evaporated under reduced pressure and the residue dissolved with EtOAc/water. The organic layer is separated, dried and evaporated under reduce pressure to give a residue that is purified by flash chromatography (eluent 0-30% EtOAc/cyclohexane) to furnish 4-methyl-3-(2-oxo-propyl)-pyridine-2-carboxylic acid tert-butylamide (2.61 g, 78%).

Workup

  1. customVolatiles are evaporated under reduced pressure
  2. dissolutionthe residue dissolved with EtOAc/water
  3. customThe organic layer is separated
  4. customdried
  5. customevaporated
  6. customto give a residue that
  7. customis purified by flash chromatography (eluent 0-30% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-d17c3b2ebf65457d9280d172a78fad6e
Source dataset
uspto-grants-2016_06
Patent number
US09371282B2

Reaction notes

Loading…