3-Ethyl-1-pentyn-3-ol → HCID 19851524, compound

HRID 1607001Notes

Reaction equation

HRID 1607001 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.[CH2:19]([C:21]([OH:26])([CH2:24][CH3:25])[C:22]#[CH:23])[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>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:20]#[C:19][C:21]([CH2:24][CH3:25])([OH:26])[CH2:22][CH3:23])=[C:10]3[CH2:9][N:8]([CH3:16])[C:7](=[O:17])[C:6]=2[CH:18]=1

Participants

6

Reactant 2

HCID 226983-Ethyl-1-pentyn-3-ol2×HCID 198306858-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 19851524HCID 19851524, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 178418476HCID 178418476, compoundCatalyst2×HCID 8021DiethylamineSolvent

Procedure

8.93 g (25 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 for 24 hours with 3.03 g (27 mmol) of 3-ethyl-1-pentyn-3-ol, 100 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 20 mg of copper(I) iodide in 60 ml of diethylamine. A further 0.87 g (7.7 mmol) of 3-ethyl-1-pentyn-3-ol as well as 50 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 50 mg of copper(I) iodide were added thereto and the mixture was stirred at the boiling temperature for 0.5 hour. The reaction mixture was subsequently evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. After decolorizing the crude product with active charcoal and crystallization from ethyl acetate there was obtained 8-fluoro-3-(3-ethyl-3-hydroxy-1-pentynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 135° -136°.

Workup

  1. customThe reaction mixture was subsequently evaporated
  2. customthe residue was chromatographed on silica gel
  3. washwhile eluting with ethyl acetate
  4. customwith active charcoal and crystallization from ethyl acetate

Sources & evidence

ORD record
ord-e9ce363e176b4677bfe83ef9b1ab9147
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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