Water → HCID 90239225, compound

HRID 1051969Notes

Reaction equation

HRID 1051969 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[H-].[Na+].O>C1COCC1.CS(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 14751282-(6-Chloropyridin-3-yl)acetonitrile

Product 1

HCID 90239225HCID 90239225, compound

Reagents, catalysts & solvents 1

HCID 21830753dimethylsulfoxide THFSolvent

Procedure

To a mixture of 2-(6-chloropyridin-3-yl)acetonitrile (26.2 mmol) and 1,5-dibromopentane (26.2 mmol) in THF/DMSO (1:1, 300 mL) was added NaH (60% in mineral oil, 55.1 mmol) portionwise at 0° C. over 45 min. The mixture was allowed to warm to RT and stirred for 1 h 45 min. The reaction mixture was poured into water and extracted with DCM. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. The residue was purified by means of CC (10-80% EtOAc/Hept) to provide a colorless solid.

Workup

  1. extractionextracted with DCM
  2. washlayers were washed with brine
  3. dry with materialdried over MgSO4
  4. customThe residue was purified by means of CC (10-80% EtOAc/Hept)
  5. customto provide a colorless solid

Sources & evidence

ORD record
ord-ff6ed8d26b384f08bed18b57b6a0cd3e
Source dataset
uspto-grants-2016_07
Patent number
US09388198B2

Reaction notes

Loading…