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

HRID 1607011Notes

Reaction equation

HRID 1607011 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[N:8]([CH3:17])[CH2:7][C:6]=12.[CH:18]#[C:19][CH3:20]>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>[CH3:17][N:8]1[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:5]2[CH:4]=[N:3][C:2]([C:18]#[C:19][CH3:20])=[C:6]2[CH2:7]1

Participants

6

Reactant 2

HCID 6335PropyneHCID 198306774,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515514,5-dihydro-5-methyl-3-(1-propynyl)-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

6.78 g (20 mmol) of 4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to 100° in a pressure tube overnight with 80 mg of bis-(triphenylphosphine)-palladium(II) dichloride, 30 mg of copper(I) iodide and about 2 ml of propyne in 60 ml of diethylamine. The reaction mixture was then evaporated and the residue was chromatographed on 300 g of silica gel while eluting with ethyl acetate. By recrystallization of the crude product from ethanol there was obtained 4,5-dihydro-5-methyl-3-(1-propynyl)-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 206°-207°.

Workup

  1. customThe reaction mixture was then evaporated
  2. customthe residue was chromatographed on 300 g of silica gel
  3. washwhile eluting with ethyl acetate
  4. customBy recrystallization of the crude product from ethanol

Sources & evidence

ORD record
ord-50ed12bad2f84102815c7b436e329bac
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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