5-Methyl-2-furanboronic Acid → 2-Chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-4-(5-methyl-2-furanyl)benzenesulfonamide

HRID 130472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130472
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][C@H:22]([CH3:24])[NH:21][C@H:20]([CH3:25])[CH2:19]3)[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])(=[O:10])=[O:9])=[C:4]([Cl:28])[CH:3]=1.[CH3:29][C:30]1[O:34][C:33](B(O)O)=[CH:32][CH:31]=1.CC(C)([O-])C.[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:28][C:4]1[CH:3]=[C:2]([C:33]2[O:34][C:30]([CH3:29])=[CH:31][CH:32]=2)[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C:12]1[CH:17]=[C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[NH:21][C@H:20]([CH3:25])[CH2:19]2)[CH:15]=[CH:14][C:13]=1[O:26][CH3:27])(=[O:10])=[O:9]

Komponenten

7

Edukt 3

HCID 27343725-Methyl-2-furanboronic AcidHCID 23665647Potassium tert-butoxideHCID 590070594-Bromo-2-chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

Produkt 1

HCID 248035122-Chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-4-(5-methyl-2-furanyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 4-bromo-2-chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide (E104) (220 mg, 0.45 mmol), (5-methyl-2-furanyl)boronic acid (113 mg, 0.90 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) in DME (3 ml) was added potassium tert-butoxide (454 mg, 4.10 mmol) in water (1 ml), and the reaction heated in the microwave (set at high absorbance) at 100° C. for 30 minutes. The reaction was poured on to the SCX column eluting first with methanol and then 2M ammonia in methanol. The basic fractions were combined and solvent evaporated in vacuo. The product was purified by mass directed autoprep HPLC, the relevant fractions collected and solvent evaporated in vacuo. The product was triturated in ether to give the title compound (E306). MS (ES+) m/e 490/492 [M+H]+.

Aufarbeitung

  1. additionThe reaction was poured on to the SCX column
  2. washeluting first with methanol
  3. customsolvent evaporated in vacuo
  4. customThe product was purified by mass
  5. customthe relevant fractions collected
  6. customsolvent evaporated in vacuo
  7. customThe product was triturated in ether

Quellen und Nachweise

ORD-Eintrag
ord-cdab8c98b2b046eaac1f82220e05b452
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381728B2

Notizen zur Reaktion

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