Sodium Iodide → HCID 131736123, compound

HRID 1052381Notes

Reaction equation

HRID 1052381 reaction equation
Br[C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=[N:6]2.[I-:28].[Na+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[I:28][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=[N:6]2

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 131736124(S)-tert-Butyl (1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

Product 1

HCID 131736123HCID 131736123, compoundYield 128.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

(S)-tert-Butyl (1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (1 g, 2.31 mmol) was dissolved in 25 mL anhydrous dioxane in a Schlenk vessel. Sodium iodide (1.38 g, 3.9 mmol), copper(I) iodide (0.13 g, 0.68 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.2 g, 1.41 mmol) were added under argon conditions and the mixture was further submitted to three vacuum-argon cycles. The reaction vessel was sealed and the mixture was heated at 120° C. for 7 h. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered through celite. The organic phase was washed with 1N hydrochloric acid, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain 1.43 g (88% yield) of the title compound as a oil. Purity 68%.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through celite
  4. washThe organic phase was washed with 1N hydrochloric acid, water, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4b62f69b8220441190ff9bd0defdfbe3
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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