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Potassium Carbonate → Tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate

HRID 711264
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 711264
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].Br[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1.CN[C@@H]1CCCC[C@H]1NC>C1(C)C=CC=CC=1.[Cu]I.C(OCC)(=O)C>[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:5]=[CH:4][N:3]1[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1
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Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 234369504-Bromo-2-(trifluoromethyl)pyridineHCID 426256764-(Boc-aminomethyl)-1H-pyridin-2-one

Produkt 1

HCID 86679722Tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a reaction vessel containing a stir bar was charged with tert-butyl (2-oxo-1,2-dihydropyridin-4-yl)methylcarbamate 56-4 (72 mg, 0.32 mmol), CuI (12 mg, 0.06 mmol), and K2CO3 (88 mg, 0.64 mmol). The reaction vessel was evacuated and backfilled with nitrogen. A solution of 4-bromo-2-(trifluoromethyl)pyridine 56-5 (94 mg, 0.42 mmol) and (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (9 mg, 0.06 mmol) in toluene (3 mL) was added via syringe. The reaction was stirred at room temperature for 20 minutes, then 110° C. overnight. The reaction mixture was diluted into ethyl acetate and filtered through celite pad to remove salt. The filtrate was dried and the residue was purified by silica gel flash chromatography, and eluted with 50% ethyl acetate to give tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate 56-6. MS m/z 370.2 (M+1).

Aufarbeitung

  1. additionTo a reaction vessel containing a stir bar
  2. customThe reaction vessel was evacuated
  3. custom110° C. overnight
  4. filtrationfiltered through celite pad
  5. customto remove salt
  6. customThe filtrate was dried
  7. customthe residue was purified by silica gel flash chromatography
  8. washeluted with 50% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-da3c63718785472e9f72f994ddba510e
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181235B2

Notizen zur Reaktion

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