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

HRID 1493124Notes

Reaction equation

HRID 1493124 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[N:9]([CH3:17])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3I)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:19][CH:20]([OH:23])[C:21]#[CH:22]>C(NCC)C.C(Cl)CCl.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:1][C:2]1[C:7]2[C:8](=[O:18])[N:9]([CH3:17])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:22]#[C:21][CH:20]([OH:23])[CH3:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 162393-Butyn-2-olHCID 198306597-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198306467-chloro-4,5-dihydro-3-(3-hydroxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 111,2-DichloroethaneSolventHCID 8021DiethylamineSolvent

Procedure

7.47 g (20 mmol) of 7-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-6-one were heated to boiling under reflux for 4 hours with 1.75 g (25 mmol) of 3-butyn-2-ol, 70 mg of bis-(triphenyl -phosphine)-palladium(II) dichloride and 10 mg of copper(I) iodide in 50 ml of diethylamine and 20 ml of ethylene chloride. After evaporation of the solvent the residue was taken up in methylene chloride and the resulting suspension was suction filtered. The material obtained was washed with methylene chloride and, after recrystallization from ethyl acetate, there was obtained 7-chloro -4,5-dihydro-3-(3-hydroxy-1-butynyl)-5-methyl-6H-imidazo -[1,5-a][1,4]benzodiazepin-6-one of melting point 251-252° C.

Workup

  1. customAfter evaporation of the solvent the residue
  2. filtrationsuction filtered
  3. customThe material obtained
  4. washwas washed with methylene chloride
  5. customafter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3c310501b7a5410fa0d8c38210d1187f
Source dataset
uspto-grants-1991_06
Patent number
US05021411

Reaction notes

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