Sodium Carbonate → HCID 57682658, Verbindung

HRID 494235

Reaktionsgleichung

Reaktionsgleichung von HRID 494235
Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CCOC(C)=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>[CH3:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[N:16]4)=[CH:11][CH:10]=3)=[O:7])=[CH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 8314084-bromo-N-quinolin-7-ylbenzamideHCID 27339503-Tolylboronic acid

Produkt 1

HCID 57682658HCID 57682658, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-N-quinolin-7-ylbenzamide (Example 82) (50 mg, 0.153 mmol) in toluene (2 ml) and ethanol (0.4 ml) under an argon atmosphere was added 3-methyl-phenylboronic acid (21 mg, 0.153 mmol), 2M sodium carbonate solution (0.15 ml) and tetrakis(triphenylphosphine)palladium (0) (5 mg, 0.05 mmol). The reaction was heated at reflux for 18 h, then cooled to room temperature and diluted with EtOAc. The mixture was washed with sat. aq. sodium bicarbonate solution and water, dried over MgSO4 and concentrated to give the crude product which was purified by SPE column chromatography. Elution with 50% EtOAc in 40-60° C. petroleum ether gave the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.92 (dd, 1H), 8.19 (d, 1H), 8.13 (m, 3H), 8.01, (d, 2H), 7.86 (d, 1H), 7.75 (d, 2H), 7.46 (m, 2H), 7.36 (m, 2H), 7.25 (m, 1H), 2.46 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. washThe mixture was washed with sat. aq. sodium bicarbonate solution and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by SPE column chromatography
  8. washElution with 50% EtOAc in 40-60° C. petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-8a2189149040474f9364358f1f78d27b
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538121B2

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