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

HRID 2178738노트

반응식

HRID 2178738 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-00b28203e81b4c78bc2f9352b24d6721
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067947B2

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