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Potassium Carbonate → Tert-butyl 4-((4-(4-chlorophenyl)-6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate

HRID 629622
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 629622
Br[CH2:2][C:3]1[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2[CH:5]=[C:6]([F:9])[N:7]=[CH:8][C:3]=2[CH2:2][N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)=[CH:11][CH:12]=1
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 672273415-(Bromomethyl)-4-(4-chlorophenyl)-2-fluoropyridine

Produkt 1

HCID 67227318Tert-butyl 4-((4-(4-chlorophenyl)-6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A mixture of EXAMPLE 307B (1.24 g), tert-butyl piperazine-1-carboxylate (0.768 g), and potassium carbonate (0.570) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel using 10% ethyl acetate in hexanes to give the title compound.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with flash column chromatography on silica gel using 10% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4521be0a2bff4604b5605df7a8975847
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315488B2

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