2-Methyl-3-butyn-2-ol → 7-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606970노트

반응식

HRID 1606970 반응식
Br[C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=3[C:9](=[O:17])[N:8]([CH3:18])[CH2:7][C:6]=12.[CH3:19][C:20]([OH:24])([C:22]#[CH:23])[CH3:21]>C(NCC)C.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:16][C:15]1[C:10]2[C:9](=[O:17])[N:8]([CH3:18])[CH2:7][C:6]3[N:5]([CH:4]=[N:3][C:2]=3[C:23]#[C:22][C:20]([OH:24])([CH3:21])[CH3:19])[C:11]=2[CH:12]=[CH:13][CH:14]=1

참가 물질

7

반응물 2

HCID 82582-Methyl-3-butyn-2-olHCID 198515903-bromo-7-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

생성물 1

HCID 198306547-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6344Dichloromethane용매HCID 8021Diethylamine용매

실험 절차

3.26 g (10 mmol) of 3-bromo-7-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to boiling under reflux overnight with 1.10 g (12 mmol) of 2-methyl-3-butyn-2-ol, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 10 mg of copper(I) iodide in 20 ml of diethylamine and 15 ml of methylene chloride. The reaction mixture was evaporated and the residue was dissolved in methylene chloride. After chromatography of the solution on silica gel while eluting with ethyl acetate and crystallization from ethyl acetate there was obtained 7-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 194°-195°.

후처리

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washAfter chromatography of the solution on silica gel while eluting with ethyl acetate and crystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-0a1f3d88acff4796ba8dafac7984f941
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863920

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