Cesium carbonate → 8-bromo-6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

HRID 1485414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485414
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][CH2:8][NH:7][C:6]=2[CH:16]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>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]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][CH2:8][N:7]([C:21]3[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=3)[C:6]=2[CH:16]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 709790238-bromo-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

Produkt 1

HCID 709789288-bromo-6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepineAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 8-bromo-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (50 mg, 0.17 mmol), 1-chloro-4-iodobenzene (82 mg, 0.34 mmol), Pd2(dba)3 (15 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (15 mg) and Cs2CO3 (110 mg, 0.34 mmol) in toluene (10 mL) was heated at 110° C. overnight. The reaction mixture was evaporated, water (10 mL) was added, extracted with ethyl acetate (20 mL), concentrated to give the crude product, which was purified by prep-TLC (DCM:MeOH=15:1) to afford 8-bromo-6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (14 mg, yield 20%).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. additionwater (10 mL) was added
  3. extractionextracted with ethyl acetate (20 mL)
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by prep-TLC (DCM:MeOH=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-66651edee4304c669924579db00e706e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422292B2

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