Trifluoroacetic acid → HCID 90077325, compound

HRID 1050241Notes

Reaction equation

HRID 1050241 reaction equation
F.[K].[Br:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[N:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(O)([C:17]([F:20])([F:19])[F:18])=O.FC([Si](C)(C)C)(F)F.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O.CCOC(C)=O.CCCCCC>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]([NH:9][CH:10]2[CH2:11][CH2:12]2)[C:17]([F:20])([F:19])[F:18])=[CH:13][CH:14]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 53443437Potassium fluoride, 99%, spray-driedHCID 90043147HCID 90043147, compound

Product 1

HCID 90077325HCID 90077325, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

Potassium hydrogen fluoride (0.697 g, 8.92 mmol) and N-(4-bromobenzylidene)-cyclopropanamine (2 g, 8.92 mmol) were dissolved in acetonitrile (17.85 ml) and cooled to 0° C. TFA (1.031 ml, 13.39 mmol) was added and the reaction was stirred for 5 min. Then (trifluoromethyl)trimethylsilane (2.64 ml, 17.85 mmol) was added and the reaction was allowed to stir at rt overnight. Saturated Na2CO3 was added to the reaction mixture and the reaction stirred 5 min, then diluted with water and EtOAc/Hexane (1:1). The aqueous phase was extracted with EtOAc (×2), and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 2% to 25% EtOAc:Hexane to give product. A second purification was performed on this product on a Biotage™ 100 g column by eluting with 2% to 25% EtOAc to provide the desired product. LC-MS: calculated for C11H11BrF3N 293.00 observed m/e: 294.15 (M+H)+ (Rt 1.23/2 min).

Workup

  1. stirringto stir at rt overnight
  2. stirringthe reaction stirred 5 min
  3. extractionThe aqueous phase was extracted with EtOAc (×2)
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography on a Biotage™ 50 g column
  9. washby eluting with 2% to 25% EtOAc
  10. customHexane to give product
  11. customA second purification
  12. washby eluting with 2% to 25% EtOAc

Sources & evidence

ORD record
ord-78e06793ecd5482a8482db8a97b49cfd
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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