Dimethylformamide → HCID 86690480, compound

HRID 1026755Notes

Reaction equation

HRID 1026755 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9])[CH:3]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[C:14]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9])[CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86690481HCID 86690481, compound

Product 1

HCID 86690480HCID 86690480, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-bromo-N-propylpyridine-2-carboxamide (450 mg), phenylboronic acid (330 mg), potassium carbonate (380 mg), tetrakis(triphenylphosphine)palladium (210 mg), dimethylformamide (6.5 mL) and ethanol (3.5 mL) was stirred under irradiation with microwave while heating at 150° C. for 10 min. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic phase was washed with water and brine, and then dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=67:33-50:50) to afford 4-phenyl-N-propylpyridine-2-carboxamide (390 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=67:33-50:50)

Sources & evidence

ORD record
ord-3536f8563c4743a7ac201efcf54a0535
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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