Tetrahydrofuran → 3-Bromo-5-(oxetan-3-YL)pyridine

HRID 712698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712698
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[N:6][CH:7]=1.Cl.N[C@@H]1CC[CH2:16][CH2:15][C@H:14]1[OH:19].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.IC1COC1>CC(O)C.[Ni](I)I>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:15]2[CH2:14][O:19][CH2:16]2)[CH:3]=1

Komponenten

8

Edukt 5

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 38148115-Bromopyridine-3-boronic acidHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 133566863-Iodooxetane

Produkt 1

HCID 726987543-Bromo-5-(oxetan-3-YL)pyridineAusbeute 476,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 26038Nickel(II) iodideKatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (5-bromopyridin-3-yl)boronic acid (330 mg, 1.6 mmol), nickel(II) iodide (15 mg, 0.049 mmol), trans-2-amino-cyclohexanol hydrochloride (7 mg, 0.049 mmol) and sodium bis(trimethylsilyl)amide solution in THF (1M; 1.6 mL, 1.6 mmol) in 2-propanol (2 mL) is stirred under Ar for 10 min. 3-Iodo-oxetane (150 mg, 0.82 mmol) is added and the mixture is heated at 80° C. for 90 min. After cooling to room temperature, the mixture is filtered through diatomaceous earth, rinsing thoroughly with EtOH. The filtrate is concentrated to give crude product. Purification by flash column chromatography affords 50 mg of 3-bromo-5-oxetan-3-yl-pyridine.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture is filtered through diatomaceous earth
  3. washrinsing thoroughly with EtOH
  4. concentrationThe filtrate is concentrated
  5. customto give crude product
  6. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bfb89af1a6c44c53a905cb7349fb853d
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181272B2

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