2-Propanethiol → 5-iso-Propylthiomethyl-pyridine-2-carbonitrile

HRID 1190958Notes

Reaction equation

HRID 1190958 reaction equation
[CH3:1][CH:2]([SH:4])[CH3:3].Br[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCCCCC.CCOC(C)=O>[CH:2]([S:4][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=1)([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 10796Cesium carbonateHCID 219277275-(Bromomethyl)pyridine-2-carbonitrile

Product 1

HCID 584955955-iso-Propylthiomethyl-pyridine-2-carbonitrileYield 77.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Add 2-propanethiol (0.53 mL, 5.6 mmol) to a slurry of 5-bromomethyl-pyridine-2-carbonitrile (1.1 g, 5.6 mmol) and cesium carbonate (1.8 g, 5.6 mmol) in DMF (10 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 16 h at room temperature. Dilute the mixture with hexane/EtOAc (1:1, 100 mL) and wash with 5% aqueous NaCl (3×30 mL). Collect the organic phase, concentrate in vacuo and purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (20:1 to 7:3 gradient) to obtain the desired intermediate (0.83 g, 77%). MS (ES+) m/z: 193.2 (M+H)+.

Workup

  1. washwash with 5% aqueous NaCl (3×30 mL)
  2. customCollect the organic phase
  3. concentrationconcentrate in vacuo
  4. custompurify the residue by chromatography on silica gel (40 g)
  5. washeluting with hexane/EtOAc (20:1 to 7:3 gradient)

Sources & evidence

ORD record
ord-8231a51686d748e3b21137fd2aa9d448
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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