Toluene → 3-chloro-6-(2-triphenyleneyl)-[1]Benzothieno[2,3-c]pyridine

HRID 1848956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848956
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[S:8][C:9]3[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=3[C:4]=2[CH:3]=1.[CH:16]1[C:33]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][C:17]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[S:8][C:9]3[CH:14]=[CH:13][C:12]([C:29]4[CH:30]=[CH:31][C:32]5[C:33]6[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=6)[C:21]6[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=6)[C:27]=5[CH:28]=4)=[CH:11][C:10]=3[C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 59805119Triphenylen-2-ylboronic acidHCID 866435773-Chloro-6-bromo-[1]benzothieno[2,3-c]pyridine

Produkt 1

HCID 866435763-chloro-6-(2-triphenyleneyl)-[1]Benzothieno[2,3-c]pyridineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

The mixture of 3-chloro-6-bromo-[1]benzothieno[2,3-c]pyridine (1.7 g, 5.8 mmol), triphenylen-2-ylboronic acid (1.6 g, 5.8 mmol), potassium phosphate tribasic (3.7 g, 17 mmol), 200 mL toluene and 10 mL water was prepared and bubbled with nitrogen for twenty minutes. Then the tris(dibenzylideneacetone)dipalladium (53 mg, 0.060 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (96 mg, 0.23 mmol) were added. The mixture was bubbled with nitrogen for another twenty minutes. After refluxed overnight under nitrogen, then reaction mixture was cooled to room temperature and filtered through a silica plug and washed with dichloromethane. The first several portions were discarded since they only contained impurities. The combined filtrate was concentrated to give crude product, which was recrystallized from hot dichloromethane and hexanes to give 1.8 g 3-chloro-6-(2-triphenyleneyl)-[1]Benzothieno[2,3-c]pyridine as yellow solid (4.0 mmol, 70% yield).

Aufarbeitung

  1. customwas prepared
  2. custombubbled with nitrogen for twenty minutes
  3. customThe mixture was bubbled with nitrogen for another twenty minutes
  4. temperatureAfter refluxed overnight under nitrogen
  5. customreaction mixture
  6. filtrationfiltered through a silica plug
  7. washwashed with dichloromethane
  8. concentrationThe combined filtrate was concentrated
  9. customto give crude product, which
  10. customwas recrystallized from hot dichloromethane and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-661b6b06ede444cfb801494f7e2323f7
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952363B2

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