Dichloromethane → 5-Cyclopropylnicotinonitrile

HRID 717543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717543
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH:15]=1)[C:13]#[N:14].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.C(Cl)Cl>O1CCOCC1.O>[CH:16]1([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:15]=2)[C:13]#[N:14])[CH2:18][CH2:17]1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 7367935-BromonicotinonitrileHCID 2760897Cyclopropylboronic acid

Produkt 1

HCID 574196235-Cyclopropylnicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Cesium carbonate (20.8 g, 0.064 mol) was added to a stirred solution of 5-bromonicotinonitrile (6 g, 0.0322 mol) and cyclopropylboronic acid (2.8 g, 0.032 mol) in a mixture of 1,4-dioxan (100 mL) and water (50 mL). The reaction vessel was purged with argon for 20 min and Pd(dppf)2Cl2.DCM (1.3 g, 0.0016 mol) was added to the reaction mixture. The reaction vessel was purged again with argon for 10 min and subsequently allowed to stir at 100° C. for 3 h. The reaction mixture was filtered through a filter bed of CELITE and the filter bed was thoroughly washed with ethyl acetate (3×200 mL). The collected organic fractions were concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford 5-cyclopropylnicotinonitrile. MS (M+1): 144.8.

Aufarbeitung

  1. customThe reaction vessel was purged with argon for 20 min
  2. customThe reaction vessel was purged again with argon for 10 min
  3. filtrationThe reaction mixture was filtered through a filter bed of CELITE
  4. washthe filter bed was thoroughly washed with ethyl acetate (3×200 mL)
  5. concentrationThe collected organic fractions were concentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0c5065dceb274b0ca0f06e8f580cd736
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193724B2

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