1-Bromo-2,3-dichlorobenzene → 1-(2,3-Dichlorophenyl)-[1,4]diazepine

HRID 16119

反応式

HRID 16119 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[Cl:9].C(OC([N:17]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=[CH:18]1)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1>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]>[Cl:9][C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[N:20]1[CH:21]=[CH:22][CH:23]=[N:17][CH:18]=[CH:19]1

参加物

6

反応物 3

HCID 420661-Bromo-2,3-dichlorobenzeneHCID 57499755[1,4]Diazepine-1-carboxylic acid tert-butylesterHCID 86595863(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl

生成物 1

HCID 686314891-(2,3-Dichlorophenyl)-[1,4]diazepine

試薬・触媒・溶媒 2

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

実験手順

2.25 g (10 mmol) 1-bromo-2,3-dichloro-benzene was dissolved in dry toluene (50 ml), 2.3 (11 mmol) of [1,4]diazepine-1-carboxylic acid tert-butylester was added followed by 0.2 g BINAP (2,2-bis(diphenylphosphino)-1,1′-binaphtyl), 85 mg tris(dibenzylideneacetone)dipalladium(0) and 1.2 g (12 mmol) sodium-tert-butoxyde. The reaction mixture was refluxed for eight hours and filtered. The organic layer was washed with water, dried and evaporated in vacuo. The residue was purified by chromatography and deprotected at 10° C. using 20 ml ethylacetate saturated with gaseous hydrochloric acid, the precipitate was filtered giving 2.1 g (yield: 75%) hydrochloride salt of the title compound, melting at 182-3° C.

後処理

  1. temperatureThe reaction mixture was refluxed for eight hours
  2. filtrationfiltered
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography
  7. customdeprotected at 10° C.
  8. filtrationthe precipitate was filtered

出典と根拠

ORDレコード
ord-7a73e7e5afb045feb1e989fcb8ce389d
出典データセット
uspto-grants-2010_06
特許番号
US07737142B2

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