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 1485414노트

반응식

HRID 1485414 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 709789288-bromo-6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine수율 21.1%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-66651edee4304c669924579db00e706e
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422292B2

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