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 1485414ノート

反応式

HRID 1485414 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-66651edee4304c669924579db00e706e
出典データセット
uspto-grants-2016_08
特許番号
US09422292B2

反応ノート

読み込み中…