Cesium carbonate → 2-(3-Azido-1-trifluoromethylpropoxy)-6-trifluoromethylnicotinonitrile

HRID 1243620Notes

Reaction equation

HRID 1243620 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N:14]([CH2:17][CH2:18][CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])=[N+:15]=[N-:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[N:14]([CH2:17][CH2:18][CH:19]([C:20]([F:21])([F:23])[F:22])[O:24][C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])=[N+:15]=[N-:16]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrileHCID 219283544-Azido-1,1,1-trifluoro-2-butanol

Product 1

HCID 219283362-(3-Azido-1-trifluoromethylpropoxy)-6-trifluoromethylnicotinonitrileYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-6-(trifluoromethyl)nicotinonitrile (0.675 g, 3.27 mmol) and 4-azido-1,1,1-trifluoro-2-butanol (0.552 g, 3.26 mmol) in DMF (8.5 mL) was treated with caesium carbonate (2.18 g, 6.69 mmol) at ambient temperature. After 20 h, the mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were washed (water, brine), dried, and-evaporated to give the product as a brown oil (1.01 g, 90%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic extracts were washed (water, brine)
  3. customdried
  4. custom-evaporated

Sources & evidence

ORD record
ord-c7c80fe92c97454280168ccbf73daee0
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

Loading…