3-Methoxypropyne → 7-chloro-4,5-dihydro-3-(3-methoxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606988Notes

Reaction equation

HRID 1606988 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.[CH2:19]([O:22][CH3:23])[C:20]#[CH:21]>C(NCC)C.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:21]#[C:20][CH2:19][O:22][CH3:23])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 693933-MethoxypropyneHCID 198306597-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515797-chloro-4,5-dihydro-3-(3-methoxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 3

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

Procedure

10.0 g (26.7 mmol) of 7-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 140 mg of bis-(triphenylphosphine)-palladium(II) dichloride, 40 mg of copper(I) iodide and 3.4 ml (40.3 mmol) of methyl propargyl ether in 100 ml of diethylamine were heated to boiling under reflux for 3.5 hours. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. After recrystallization from ethyl acetate there was obtained 7-chloro-4,5-dihydro-3-(3-methoxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 154°-156°.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. customThe reaction mixture was evaporated
  3. customthe residue was chromatographed on silica gel
  4. washwhile eluting with ethyl acetate
  5. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-26435263b62e461fb71b0d28a4a5b1d3
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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