3,3-Dimethyl-1-butyne → HCID 19851576, compound

HRID 1606973Notes

Reaction equation

HRID 1606973 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][C:20]([CH3:24])([CH3:23])[C:21]#[CH:22]>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:22]#[C:21][C:20]([CH3:24])([CH3:23])[CH3:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 135123,3-Dimethyl-1-butyneHCID 198306597-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 19851576HCID 19851576, compound

Reagents, catalysts & solvents 3

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

Procedure

3.73 g (10 mmol) of 7-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was stirred at the boiling temperature for 24 hours with 1.46 ml (12 mmol) of 3,3-dimethyl-1-butyne, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 10 mg of copper(I) iodide in 30 ml of diethylamine. After evaporation of the reaction mixture the residue was taken up in methylene chloride and washed twice with water. The organic phase was dried over magnesium sulphate, evaporated and the residue was chromatographed on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1). After crystallization from ethyl acetate and hexane there was obtained 7-chloro-3-(3,3-dimethyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 126°-128°.

Workup

  1. customAfter evaporation of the reaction mixture the residue
  2. washwashed twice with water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated
  5. customthe residue was chromatographed on silica gel
  6. washwhile eluting with cyclohexane/ether/isopropanol (3:3:1)
  7. customAfter crystallization from ethyl acetate

Sources & evidence

ORD record
ord-bcccd3c4200a42fbbd0d78b174aae304
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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