Cesium carbonate → (+/-)-2'-(1-Cyano-2,2-dipyridin-3-ylethyl)-1,1'-biphenyl-3-carbonitrile

HRID 1686080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1686080
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH:11]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[C:9]#[N:10].[C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)#[N:25].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[C:9]([CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([C:24]#[N:25])[CH:31]=1)[CH:11]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)#[N:10]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 672655872-(2-Bromophenyl)-3,3-dipyridin-3-ylpropanenitrile

Produkt 1

HCID 57867552(+/-)-2'-(1-Cyano-2,2-dipyridin-3-ylethyl)-1,1'-biphenyl-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 2-(2-bromophenyl)-3,3-dipyridin-3-ylpropanenitrile (0.050 g, 0.137 mmol), 3-cyanophenylboronic acid (0.030 g, 0.206 mmol), cesium carbonate (0.045 g, 0.137 mmol) and Pd(dppf)2 (0.100 g, 0.137 mmol) in THF (0.75 mL) and water (0.75 mL) at −78° C. was heated to 160° C. in microwave for 15 min. The reaction was diluted with water and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give (±)-2′-(1-cyano-2,2-dipyridin-3-ylethyl)-1,1′-biphenyl-3-carbonitrile. 1H-NMR (500 MHz, CDCl3) δ 8.57 (d, 1H, J=3.9), 8.45 (d, 1H, J=4.2), 8.42 (s, 1H), 7.88 (s, 1H), 7.71 (m, 1H), 7.66-7.56 (m, 3H), 7.51 (td, 1H, J=7.5, 1.2), 7.41 (td, 1H, J=7.6, 1.3), 7.34-7.32 (m, 2H), 7.18-7.07 (m, 3H), 7.00 (d, 1H, J=7.8), 4.57 (d, 1H, J=10.0), 4.33 (d, 1H, J=9.8). LRMS m/z (M+H) Calcd: 387.1604, found: 387.1592.

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. customThe combined organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-b1118cc6bec9424fbfe6b561c645db56
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148535B2

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