Sodium Carbonate → 1-[6-[3-(4-Morpholinyl)-5-nitrophenyl]-2-pyridinyl]cyclobutanol

HRID 2207352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207352
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[N:13]=[C:12]([C:14]2([OH:18])[CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=1.[N+:19]([C:22]1[CH:23]=[C:24]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:25]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=1)([O-:21])=[O:20]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[N:37]1([C:24]2[CH:25]=[C:26]([C:8]3[N:13]=[C:12]([C:14]4([OH:18])[CH2:17][CH2:16][CH2:15]4)[CH:11]=[CH:10][CH:9]=3)[CH:27]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 589324181-(6-Bromopyridin-2-yl)cyclobutanolHCID 672568704-(3-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

Produkt 1

HCID 1180930551-[6-[3-(4-Morpholinyl)-5-nitrophenyl]-2-pyridinyl]cyclobutanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418807HCID 178418807, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Pd(dppf)Cl2-dichloromethane adduct (40.8 mg, 0.05 mmol) and sodium carbonate (2 N, 1.5 mL, 3.0 mmol) were added to 1-(6-bromopyridin-2-yl)cyclobutanol (228 mg, 1.0 mmol) and 4-[3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (0.2 N in DMF, 5.0 mL, 1.0 mmol) and the reaction mixture was purged and flushed with N2(g) (3×). The reaction mixture was heated to 100° C. for 4 hours, then cooled to room temperature, diluted with water, extracted with diethyl ether, washed with brine, dried over sodium sulfate, filtered an concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate:hexanes) to afford 1-{6-[3-(morpholin-4-yl)-5-nitrophenyl]pyridin-2-yl}cyclobutanol. 1H NMR (500 MHz, CDCl3) δ 8.30-8.23 (m, 1H), 7.98-7.95 (m, 1H), 7.93, (t, J=7.2 Hz 1H), 7.79 (t, J=2.2, 1H), 7.74 (d, J=7.8, 1H), 7.66 (d, J=7.8, 1H), 5.36 (s, 1H), 4.03-3.84 (m, 4H), 3.46-3.29 (m, 4H), 2.82-2.47 (m, 4H), 2.27-2.09 (m, 1H), 2.05-1.91 (m, 1H).

Aufarbeitung

  1. customthe reaction mixture was purged
  2. customflushed with N2(g) (3×)
  3. temperaturecooled to room temperature
  4. additiondiluted with water
  5. extractionextracted with diethyl ether
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationan concentrated under reduced pressure
  10. customThe crude product was purified by silica gel chromatography (ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8764354602794e96b2b97a97ed28a52b
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376418B2

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