Ammonia → HCID 86708231, compound

HRID 1750056Notes

Reaction equation

HRID 1750056 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[C:4]([O-])=O.[Na+].Cl[C:13]1[CH:18]=[CH:17]C(I)=[CH:15][N:14]=1.[CH3:20][NH2:21].N.C(=O)(O)[O-].[Na+]>[Cu](I)I.C1(C)C(C)=CC=CC=1.CN1C(=O)CCC1>[CH3:20][NH:21][C:13]1[CH:18]=[CH:17][C:4]([C:3]([F:8])([F:7])[C:2]([F:10])([F:9])[F:1])=[CH:15][N:14]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 2733305Sodium pentafluoropropionateHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 86708231HCID 86708231, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 7237O-XyleneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

28 g of sodium pentafluoropropionate and 14 g of copper iodide were added to a mixture of 7.2 g of 2-chloro-5-iodopyridine, 75 ml of NMP and 75 ml of xylene under room temperature, and the mixture was heated to 150° C. and heated and stirred for 5.5 hours. After cooling the mixture to 80° C., 180 ml of an aqueous methylamine solution (40%) was added in 4 parts every 2 hours, and the mixture was heated and stirred for 8.5 hours. After the reaction, the mixture was ice-cooled to 0° C, a 28% aqueous ammonia solution and a saturated aqueous sodium bicarbonate solution were added, and the mixture was extracted with methyl tert-butyl ether (hereinafter, referred to as MTBE). The combined organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 4.6 g of methyl-(5-pentafluoroethyl-pyridin-2-yl)-amine.

Workup

  1. temperatureheated
  2. temperatureAfter cooling the mixture to 80° C.
  3. temperaturethe mixture was heated
  4. stirringstirred for 8.5 hours
  5. customAfter the reaction
  6. temperaturecooled to 0° C
  7. extractionthe mixture was extracted with methyl tert-butyl ether (hereinafter,
  8. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74986d6f50054eff9f88e4f3020022d5
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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