Diethyl Ether → (5-Chlorothiophen-2-YL)(pyridin-2-YL)methanone

HRID 900759Notes

Reaction equation

HRID 900759 reaction equation
Br[Mg][C:3]1[S:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)#N.CC[O:19]CC>>[Cl:8][C:5]1[S:4][C:3]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:19])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7522Pyridine-2-carbonitrileHCID 178478193HCID 178478193, compound

Product 1

HCID 53401492(5-Chlorothiophen-2-YL)(pyridin-2-YL)methanoneYield 52%

Procedure

To an etheral solution of bromo(5-chloro-2-thienyl)magnesium (prepared from 2-bromo-5-chloro-thiophene (1.9 g, 9.62 mmol) and magnesium turnings (234 mg, 9.62 mmol) in ether (20 ml)) was dropwise added a solution of 2-cyanopyridine (1 g, 9.62 mmol) in ether (10 ml) at room temperature. After 2 hours, the reaction was quenched by addition of an aqueous saturated solution of NH4Cl. The mixture was extracted with ether. The organic phase was dried over MgSO4 and concentrated under vacuum. The residue was treated with a 2 N HCl solution at 90° C. during 30 minutes. The solution was neutralized by addition of a concentrated solution of NaOH and extracted with ether. The organic phase was dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel (hexane/AcOEt 90/10) to give the (5-chloro-2-thienyl)(2-pyridinyl)methanone 8 as a yellowish oil (1.13 g, 52%).

Workup

  1. customthe reaction was quenched by addition of an aqueous saturated solution of NH4Cl
  2. extractionThe mixture was extracted with ether
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. additionThe residue was treated with a 2 N HCl solution at 90° C. during 30 minutes
  6. additionThe solution was neutralized by addition of a concentrated solution of NaOH
  7. extractionextracted with ether
  8. dry with materialThe organic phase was dried over MgSO4
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by chromatography on silica gel (hexane/AcOEt 90/10)

Sources & evidence

ORD record
ord-0356a6e055ba44079edbcd50f54fabfa
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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