3-Cyanophenylboronic acid → HCID 67174268, Verbindung

HRID 1408808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408808
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=[CH2:18].[C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:20]>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:18]=[C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:25]3[CH:26]=[C:21]([CH:22]=[CH:23][CH:24]=3)[C:19]#[N:20])[CH:3]=2)[O:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1

Komponenten

6

Edukt 2

HCID 27343253-Cyanophenylboronic acidHCID 58424290HCID 58424290, Verbindung

Produkt 1

HCID 67174268HCID 67174268, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 10796Cesium carbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Pd(PPh3)2Cl2 (40 mg) in a 100 mL of flask under Ar2 was treated sequentially with 6-bromo-4-methylene-2-phenylchroman (200 mg, 0.67 mmol) in [1,4]dioxane (20 mL), Cs2CO3 (2 N, 3.33 mL) and 3-cyanophenylboronic acid (167 mg, 1.13 mmol). The mixture was heated under 120 at Ar2 under microwave for 30 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified preparative TLC to give 3-(4-methylene-2-phenyl-chroman-6-yl)-benzonitrile (110 mg, 51%). 1H-NMR (CDCl3): 2.81 (m, 2H), 4.96 (d, 1H), 5.10 (m, 1H), 5.61 (d, 1H), 7.98 (d, 1H), 7.29 (m, 1H), 7.35 (m, 3H), 7.41 (m, 2H), 7.46 (m, 1H), 7.52 (m, 1H), 7.72 (m, 2H), 7.79 (d, 1H).

Aufarbeitung

  1. temperatureThe mixture was heated under 120 at Ar2 under microwave for 30 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give the residue, which
  4. customwas purified preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-1b0d95e33b4e46b9b804802acdd236dc
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921359B2

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