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Potassium Carbonate → Trifluoroacetic acid

HRID 60868
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 60868
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH3:17])[C@@H:12]1[CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1)=[O:10].[CH3:30][N:31]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1.[C:45]([O-:48])([O-])=[O:46].[K+].[K+]>O1CCOCC1.O>[CH3:17][C@H:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:9]([C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[C:34]2[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=2)=[O:10])[C@H:12]1[CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1.[C:45]([OH:48])([C:26]([F:29])([F:28])[F:27])=[O:46]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 131737147rac-cis-(2-Bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone

Produkt 2

HCID 6422Trifluoroacetic acidHCID 117727860US9896452, Ex. A315

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The mixture of rac-cis-(2-bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone (0.045 g, 0.097 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.024 g, 0.116 mmol), P(PPh3)4 (0.017 g, 0.015 mmol), K2CO3 (0.4 g, 0.291 mmol) and dioxane/H2O (4:1, 3 mL) was degassed for 5 min and heated overnight at 100° C. oil bath. The completion of reaction was monitored by analytical HPLC. The mixture was cooled and extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain a crude residue, which was purified by preparative-HPLC to obtain the title compound as TFA salt. ESI-MS (m/z): 472, [M+1]+.

Aufarbeitung

  1. customwas degassed for 5 min
  2. customThe completion of reaction
  3. temperatureThe mixture was cooled
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with saturated NaHCO3
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customto obtain a crude residue, which
  9. customwas purified by preparative-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3b156d59130a45f0b2052d7acc1ab7b1
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440982B2

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