2-Methyl-3-butyn-2-ol → HCID 19851525, compound

HRID 1606977Notes

Reaction equation

HRID 1606977 reaction equation
[Br: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]([OH:24])([C:22]#[CH:23])[CH3:21]>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>[Br: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:23]#[C:22][C:20]([OH:24])([CH3:21])[CH3:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 19830661HCID 19830661, compound

Product 1

HCID 19851525HCID 19851525, compound

Reagents, catalysts & solvents 3

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

Procedure

3.74 g (8.95 mmol) of 7-bromo-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was stirred at the boiling temperature for 1.5 hours with 0.80 g (9.5 mmol) of 2-methyl-3-butyn-2-ol, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 10 mg of copper(I) iodide in 30 ml of diethylamine. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. After recrystallization of the residue, which remains behind upon evaporation of the eluate, from ethyl acetate there was obtained 7-bromo-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 207°-208°.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on silica gel
  3. washwhile eluting with ethyl acetate
  4. customAfter recrystallization of the residue, which
  5. customremains behind upon evaporation of the eluate, from ethyl acetate

Sources & evidence

ORD record
ord-15f07b469c7942d4931361d8a31e0be1
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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