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

HRID 16119

반응식

HRID 16119 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7a73e7e5afb045feb1e989fcb8ce389d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737142B2

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