Toluene → HCID 22147975, Verbindung

HRID 1823967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823967
[CH3:1][N:2]([CH3:12])[S:3]([N:6]1[CH:10]=[C:9](Br)[N:8]=[CH:7]1)(=[O:5])=[O:4].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][N:2]([CH3:12])[S:3]([N:6]1[CH:10]=[C:9]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[N:8]=[CH:7]1)(=[O:5])=[O:4]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 221479874-Bromo-N,N-dimethyl-1H-imidazole-1-sulfonamide

Produkt 1

HCID 22147975HCID 22147975, VerbindungAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of the bromide from Step 1 (0.543 g), 4-fluorophenylboronic acid (0.31 g), tetrakis(triphenylphosphine) palladium (0) (0.2 g), 2M aqueous sodium carbonate (2.2 mL) and toluene (10 mL) was refluxed under N2 for 1.5 hours. The mixture was cooled, poured into water (75 mL) and extracted with ethyl actetate (2×25 mL). The extracts were dried over Na2SO4, filtered and concentrated. Flash column chromatography, eluting with 40% ethyl acetate-isohexane, gave 1-(dimethylaminosulfonyl)-4-(4-fluorophenyl)imidazole (0.417 g, 72%) as a yellow solid. MS (ES+) 270 ([MH]+).

Aufarbeitung

  1. temperaturewas refluxed under N2 for 1.5 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl actetate (2×25 mL)
  4. dry with materialThe extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washFlash column chromatography, eluting with 40% ethyl acetate-isohexane

Quellen und Nachweise

ORD-Eintrag
ord-a4145a78ff794ec6b59c21d8583de54f
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041689B2

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