Triethylamine → HCID 86655165, compound

HRID 1877516Notes

Reaction equation

HRID 1877516 reaction equation
[C:1]([C:3]1[C:8](F)=[CH:7][C:6]([F:10])=[CH:5][N:4]=1)#[N:2].Cl.[F:12][CH2:13][CH2:14][NH2:15].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C.O>[C:1]([C:3]1[C:8]([NH:15][CH2:14][CH2:13][F:12])=[CH:7][C:6]([F:10])=[CH:5][N:4]=1)#[N:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 11430Potassium CarbonateHCID 27832532-Cyano-3,5-difluoropyridine

Product 1

HCID 86655165HCID 86655165, compoundYield 19.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

500 mg of 2-cyano-3,5-difluoropyridine, 426 mg of 2-fluoroethylamine hydrochloride, 987 mg of potassium carbonate and 433 mg of triethylamine in 10 ml of dimethyl sulphoxide are introduced into a 20 ml microwave tube reactor. The mixture is then heated in the microwave for 1 and a half hours at 115° C. The reaction medium is run into 100 ml of water and 100 ml of ethyl acetate. The aqueous phase is re-extracted twice with 50 ml with ethyl acetate. The combined organic phases are washed with water and then with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. After purification by flash chromatography on 70 g of silica gel, elution being carried out with a mixture of ethyl acetate and cyclohexane (30/70 by volume), and the first eluted product being recovered, 125 mg of 2-cyano-5-fluoro-3-(2-fluoroethylamino)pyridine are thus obtained in the form of a white powder, the characteristics of which are the following:

Workup

  1. extractionThe aqueous phase is re-extracted twice with 50 ml with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by flash chromatography
  6. washon 70 g of silica gel, elution
  7. additionbeing carried out with a mixture of ethyl acetate and cyclohexane (30/70 by volume)
  8. customthe first eluted product being recovered

Sources & evidence

ORD record
ord-813818d23df3495c90ea93a2615f3011
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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