Dichloromethane → HCID 59007072, Verbindung

HRID 130403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130403
Br[C:2]1[N:7]=[C:6]([S:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[S:18]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19]1.ClCCl>C(=O)([O-])[O-].[Na+].[Na+].CN1CCCC1=O.O>[S:18]1[CH:22]=[CH:21][C:20]([C:2]2[N:7]=[C:6]([S:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)=[CH:19]1

Komponenten

7

Edukt 3

HCID 6344DichloromethaneHCID 581760Thiophene-3-boronic acidHCID 59007102HCID 59007102, Verbindung

Produkt 1

HCID 59007072HCID 59007072, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 10340Sodium CarbonateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of phenyl 6-bromo-2-pyridinesulfonate (D7) (1.0 g, 7.2 mmol), 3-thienylboronic acid (532 mg, 8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (80 mg) in sodium carbonate (2M solution, 5 ml) and 1-methyl-2-pyrrolidinone (8 ml) was heated at 130° C. in a microwave reactor for 5 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (1:40 to 1:5 ethyl acetate:hexanes) to afford the title product (D8). MS (ES+) m/e 318 [M+H]+.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (1:40 to 1:5 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8e470ecb1fba4f1aa3851a1d8367dc5d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381728B2

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