Pyridine → HCID 178490463, compound

HRID 2200846Notes

Reaction equation

HRID 2200846 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH3:11][O:12][C:13]1[C:18]([OH:19])=[CH:17][CH:16]=[C:15](/[CH:20]=[CH:21]/[C:22]([CH2:24][C:25](/[CH:27]=[CH:28]/[C:29]2[CH:37]=[C:34]([O:35][CH3:36])[C:32]([OH:33])=[CH:31][CH:30]=2)=[O:26])=[O:23])[CH:14]=1.O/C(/C=C/C1C=CC(O)=C(OC)C=1)=C\C(=O)/C=C/C1C=CC(O)=C(OC)C=1.N1C=CC=CC=1>C1COCC1.CCOC(C)=O>[C:2]([O:19][C:18]1[CH:17]=[CH:16][C:15](/[CH:20]=[CH:21]/[C:22](=[O:23])/[CH:24]=[C:25](\[OH:26])/[CH:27]=[CH:28]/[C:29]2[CH:30]=[CH:31][C:32]([OH:33])=[C:34]([O:35][CH3:36])[CH:37]=2)=[CH:14][C:13]=1[O:12][CH3:11])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 969516CurcuminHCID 5281767HCID 5281767, compound

Product 1

HCID 178490463HCID 178490463, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of nicotinoyl chloride hydrochloride [296] (0.725 g, 4.0 mmol, 1.5 eq) in THF (30 ml) was added TEA (1 ml, x mmol, y eq) drop-wise at 0° C. A solution of curcumin, (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one [4151] (1.0 g, 2.7 moles, 1.0 eq) and pyridine (1 ml) in THF (10 ml) was then added at the same temperature. The reaction temperature was gradually increased to RT. The reaction mixture was stirred for 20 h at RT. Reaction was monitored by TLC. The reaction mixture was diluted with EtOAc (200 ml), washed by saturated NaHCO3 solution (75 ml) and water (100 ml) successively. The EtOAc layer was separated, dried with sodium sulphate and concentrated under reduced pressure to yield a crude product. The crude product was purified by column chromatography using (2% MeOH: DCM, 100-200 mesh) get the desired product, 4-((1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trien-1-yl)-2-methoxyphenyl nicotinate [307] as yellow solid (0.30 g, 23%).

Workup

  1. customReaction
  2. washwashed by saturated NaHCO3 solution (75 ml) and water (100 ml) successively
  3. customThe EtOAc layer was separated
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a crude product
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-1c496f5711e9489abbfc41fcc16e5ceb
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

Loading…