1-Chloro-2-ethynylbenzene → 3-[(o-chlorophenyl)ethynyl]-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1607005Notes

Reaction equation

HRID 1607005 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14](I)=[C:10]3[CH2:9][N:8]([CH3:16])[C:7](=[O:17])[C:6]=2[CH:18]=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]#[CH:27]>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:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]#[C:27][C:14]1[N:13]=[CH:12][N:11]2[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:18][C:6]=3[C:7](=[O:17])[N:8]([CH3:16])[CH2:9][C:10]=12

Participants

7

Reactant 2

HCID 5859951-Chloro-2-ethynylbenzeneHCID 198306858-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515203-[(o-chlorophenyl)ethynyl]-8-fluoro-4,5-dihydro-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 6344DichloromethaneSolventHCID 8021DiethylamineSolvent

Procedure

3.6 g (10 mmol) of 8-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was stirred at room temperature overnight with 1.5 g (11 mmol) of o-chlorophenylacetylene, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 15 mg of copper(I) iodide in 20 ml of diethylamine. The reaction mixture was diluted with 175 ml of methylene chloride and washed three times with water. After drying and evaporation of the solution the residue was chromatographed on silica gel while eluting with methylene chloride/methanol (99:1). By recrystallization of the evaporated eluate there was obtained 3-[(o-chlorophenyl)ethynyl]-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 259°-261°.

Workup

  1. washwashed three times with water
  2. customAfter drying
  3. customevaporation of the solution the residue
  4. customwas chromatographed on silica gel
  5. washwhile eluting with methylene chloride/methanol (99:1)
  6. customBy recrystallization of the evaporated eluate there

Sources & evidence

ORD record
ord-4bc60bb50e384d9cad1f73349ffe154f
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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