6-Chloro-3-pyridinecarbonitrile → HCID 58495499, compound

HRID 1190960Notes

Reaction equation

HRID 1190960 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]([SH:14])[CH2:9]1.Cl[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=1>CN(C=O)C.O>[CH3:7][C:8]1([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]([S:14][C:17]2[N:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 23665647Potassium tert-butoxideHCID 58495652HCID 58495652, compound

Product 1

HCID 58495499HCID 58495499, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add potassium tert-butoxide (777 mg, 6.94 mmol) to a solution of 3,3-dimethylcyclohexanethiol (1 g, 6.94 mmol) in DMF (10 mL) and stir at room temperature for 10 min. Add 6-chloro-nicotinonitrile (547 mg, 3.96 mmol) and warm the solution to 60° C. for 18 h. Cool the mixture, dilute with water (100 mL) and extract with EtOAc (50 mL). Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to obtain the desired intermediate as a clear oil that solidifies on standing to a white solid (0.37 g, 38%).

Workup

  1. temperatureCool the mixture
  2. extractionextract with EtOAc (50 mL)
  3. dry with materialDry the organic phase over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-56497808c10c41eea570aaaeda381233
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…