Potassium Carbonate → HCID 89613316, compound

HRID 623287Notes

Reaction equation

HRID 623287 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[F:10][C:11]([F:22])([F:21])[C:12]([N:14]=[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][NH:16]1)=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][N:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]2=[N:14][C:12](=[O:13])[C:11]([F:21])([F:22])[F:10])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220506385-(Bromomethyl)-2-fluoropyridineHCID 178522125HCID 178522125, compound

Product 1

HCID 89613316HCID 89613316, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

57 mg (0.30 mmol) of the 5-bromomethyl-2-fluoropyridine obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 57 mg (0.30 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide synthesized by the method described in (1) of Synthetic Example P1 and 69 mg (0.50 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→3:1) to obtain the subject material. Amount obtained 21 mg (yield 23%).

Workup

  1. additionwere added
  2. temperaturein sequence, and the resulting mixture was heated
  3. temperaturerefluxed for 6 hours
  4. customwas returned to room temperature
  5. filtrationto filter insoluble materials
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→3:1)
  8. customto obtain the subject material
  9. customAmount obtained 21 mg (yield 23%)

Sources & evidence

ORD record
ord-d2a2e24ede454b778d1c5f7f6a56741c
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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