Cesium carbonate → 3-(3-Nitrophenylthio)pyridine

HRID 710607

Reaction equation

HRID 710607 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.O=C1CCCCC1C(OCC)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu](I)I>[N+:1]([C:4]1[CH:5]=[C:6]([S:10][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 2435763-Nitrobenzene-1-thiol

Product 1

HCID 1184923323-(3-Nitrophenylthio)pyridineYield 43.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

3-nitrophenylmercaptan (5 g, 32 mmol), 3-bromopyridine (6.1 g, 38.6 mmol), ethyl 2-oxocyclohexylformate (1.1 g, 6.5 mmol), copper iodide (608 mg, 4.2 mmol), cesium carbonate (2.3 g, 70.6 mmol) were dissolved in 500 ml of DMSO, reacted under microwaves at 100° C. for 8 h. After being extracted with water and DCM, the organic phase was dried and separated with column chromatography to obtain an object product 3.2 g.

Workup

  1. customreacted under microwaves at 100° C. for 8 h
  2. extractionAfter being extracted with water and DCM
  3. customthe organic phase was dried
  4. customseparated with column chromatography

Sources & evidence

ORD record
ord-a0d13f15a77e4ef9bae4bf6373c2ca64
Source dataset
uspto-grants-2015_11
Patent number
US09181244B1

Linked notes

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