Ethyl 4-piperidinecarboxylate → {2-[4-(Ethoxycarbonyl)piperidin-1-yl]pyrimidin-5-yl}boronic acid

HRID 626934

Reaktionsgleichung

Reaktionsgleichung von HRID 626934
Cl[C:2]1[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1>O1CCOCC1>[CH2:20]([O:19][C:17]([CH:14]1[CH2:15][CH2:16][N:11]([C:2]2[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=2)[CH2:12][CH2:13]1)=[O:18])[CH3:21]

Komponenten

4

Edukt 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

Produkt 1

HCID 131735233{2-[4-(Ethoxycarbonyl)piperidin-1-yl]pyrimidin-5-yl}boronic acidAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(2-Chloropyrimidin-5-yl)boronic acid (2 g, 13 mmol) and ethyl piperidine-4-carboxylate (1.94 mL, 13 mmol) were dissolved in 1,4-dioxane (20 mL) and heated to 60° C. under microwave irradiation for 1 h. The reaction mixture was concentrated to dryness and partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to dryness, to afford the title compound (1.79 g, 51%) as a yellow gum. Method C HPLC-MS: MH+ m/z 280, RT 0.94 minutes (89%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-887cd9ba4d444b31acc0b11e1d1fc50d
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309243B2

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