1,10-Phenanthroline → HCID 88540537, compound

HRID 1750050Notes

Reaction equation

HRID 1750050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]([OH:17])(=[S:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(N(C(C)C)CC)(C)C>[Cu](I)I.O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([S:16][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 81531DiisopropylethylamineHCID 43971762-Chloro-5-iodopyridineHCID 178526132HCID 178526132, compound

Product 1

HCID 88540537HCID 88540537, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 23.9 g of 2-chloro-5-iodopyridine, 14 ml of thiobenzoic acid, 1.90 g of copper iodide, 3.60 g of 1,10-phenanthroline, 35 ml of diisopropylethylamine and 200 ml of toluene was stirred at 110° C. for 4 hours. Water was added to the reaction mixture cooled to room temperature, and the insoluble matter was filtered with celite (registered trademark), and then the filtered matter was washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 21.2 g of thiobenzoic acid S-(6-chloropyridin-3-yl)ester.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe insoluble matter was filtered with celite (registered trademark)
  3. washthe filtered matter was washed with ethyl acetate
  4. extractionthe filtrate was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d2f1d90fa514973bffe34f33f249051
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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