3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 68814474, compound

HRID 732539Notes

Reaction equation

HRID 732539 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:16]=[C:15]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.Cl.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[N:35][CH:34]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1COCC1>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:16]=[C:15]([C:32]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[O:39])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

6

Reactant 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68815098HCID 68815098, compound

Product 1

HCID 68814474HCID 68814474, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Add THF (3 mL), N-methyl-N-propyl-5-tributylstannanyl-isophthalamic acid methyl ester (0.524 g, 1.00 mmol), nicotinoyl chloride hydrochloride (0.232 g, 1.30 mmol), 2-(di-tert-butylphosphino)biphenyl (0.045 g, 0.151 mmol), bis(dibenzylidene-acetone)palladium (0) (029 g, 0.05 mmol) to a sealed tube flushed with nitrogen. Heat the mixture at 50° C. for 16 h and cool to room temperature. Filter the mixture though a filtering agent, concentrate and purify (silica gel chromatography, eluting with 50:50 to 100:0 ethyl acetate:hexanes) to give the title compound (0.070 g, 21%).

Workup

  1. customflushed with nitrogen
  2. temperaturecool to room temperature
  3. filtrationFilter the mixture though a filtering agent
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 50:50 to 100:0 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-fa561afccb7c4bc8afa530017c13c2f6
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…