Sodium Carbonate → 9-(3-(5-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)phenyl)-9H-carbazole

HRID 520825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520825
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([N:15]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:21]4[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:12]=[CH:13][CH:14]=2)O1.Br[C:30]1[CH:31]=[C:32]([C:36]2[N:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:39]3[CH:47]=[CH:48][CH:49]=[CH:50][C:38]=3[N:37]=2)[CH:33]=[N:34][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[C:41]1([N:40]2[C:39]3[CH:47]=[CH:48][CH:49]=[CH:50][C:38]=3[N:37]=[C:36]2[C:32]2[CH:31]=[C:30]([C:13]3[CH:12]=[C:11]([N:15]4[C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[C:22]5[C:27]4=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH:10]=[CH:9][CH:14]=3)[CH:35]=[N:34][CH:33]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 230940852-(5-bromopyridine-3-yl)-1-phenyl-1H-benzimidazoleHCID 586908999-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

Produkt 1

HCID 866793109-(3-(5-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)phenyl)-9H-carbazoleAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of compound 1C (3.0 g, 8.15 mmol), compound 1F (2.85 g, 8.15 mmol), tetrakistriphenylphosphine palladium (471 mg, 0.408 mmol), and sodium carbonate (3.09 g, 29.2 mmol) in tetrahydrofuran (THF)/water (50 mL/30 mL) was degassed for about 45 minutes. The mixture then heated to reflux (about 80° C.) overnight under argon. After cooling to RT, the reaction mixture was poured into DCM (300 mL) then washed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL). The organic phase was then collected, dried over magnesium sulfate, and loaded onto silica gel. A flash column (gradient of 25% to 40% ethyl acetate in DCM) and precipitation from ethyl acetate/methanol gave 2.34 g of HTH-1; 56% yield, pure by HNMR.

Aufarbeitung

  1. customwas degassed for about 45 minutes
  2. temperatureThe mixture then heated
  3. temperatureAfter cooling to RT
  4. additionthe reaction mixture was poured into DCM (300 mL)
  5. washthen washed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL)
  6. customThe organic phase was then collected
  7. dry with materialdried over magnesium sulfate
  8. customA flash column (gradient of 25% to 40% ethyl acetate in DCM) and precipitation from ethyl acetate/methanol
  9. customgave 2.34 g of HTH-1

Quellen und Nachweise

ORD-Eintrag
ord-5ac94c479fd543a099b62b2a86a06e32
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328094B2

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