Cesium carbonate → HCID 117727942, compound

HRID 1750487Notes

Reaction equation

HRID 1750487 reaction equation
[N:1]1[NH:2][N:3]=[CH:4][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC.Br[C:23]1[C:31]([F:32])=[CH:30][CH:29]=[C:28]([F:33])[C:24]=1[C:25]([OH:27])=[O:26]>O1CCOCC1.[Cu]I.O>[F:32][C:31]1[C:23]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[C:24]([C:28]([F:33])=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 675161H-1,2,3-TriazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 144915972-Bromo-3,6-difluorobenzoic acid

Product 1

HCID 117727942HCID 117727942, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of 2H-1,2,3-triazole (CAS number 288-36-8; 0.23 g, 3.33 mmol) in 1,4-dioxane (4.0 ml) was added cesium carbonate (1.0 g, 3.33 mmol), trans-1-N,2-N-dimethylcyclohexane-1,2-diamine (0.047 g, 0.33 mmol), copper(I) iodide (0.015 g, 0.08 mmol) and 2-bromo-3,6-difluorobenzoic acid (CAS number 124244-65-1; 0.40 g, 1.68 mmol). The reaction was stirred at 120° C. for 30 minutes and was then poured into water (10 ml) and extracted with ethyl acetate (2×30 ml). The organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-5% methanol/DCM) to afford the title compound.

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. washThe organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (silica, 0-5% methanol/DCM)

Sources & evidence

ORD record
ord-21fa64ad9806483fabc5bd34def2019c
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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