N,N-Dimethylglycine → Carbazole

HRID 1486370Notes

Reaction equation

HRID 1486370 reaction equation
O1CCCCC1[N:7]1[C:19]2[CH:18]=[C:17](O)[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.BrC1C=C(N2C(C)=CC(C)=N2)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>[Cu]I.C(OCC)(=O)C.O.O1CCOCC1>[CH:9]1[C:8]2[NH:7][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 229808051-(3-Bromophenyl)-3,5-dimethyl-1H-pyrazoleHCID 68181306N-tetrahydropyranyl-2-hydroxycarbazole

Product 1

HCID 6854CarbazoleYield 79%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

In another step, 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-Netrahydropyranyl) carbazole was synthesized. To a 100 mL sealed tube was added with N-tetrahydropyranyl-2-hydroxycarbazole (880 mg, 3.0 mmol), N-(3-Bromophenyl)-3,5-dimethylpyrazole (826 mg, 3.30 mmol), Cesium carbonate (2.9 g, 3 mmol), copper(I) iodide (57 mg, 0.3 mmol), N, N-dimethylglycine (93 mg, 0.9 mmol) and 1,4-dioxane (8 mL) in glove box, and the mixture was stirred at 90° C. for 3 days. After cooling to rt, the mixture was treated with water (75 mL) and ethyl acetate (40 mL), and the water phase was extracted with ethyl acetate (3×30 mL). The organic extracted phase was combined, washed with brine (3×30 mL), dried with magnesium sulfate and concentrated. The resulting crude product was purified with an silica gel chromatography with hexane/ethyl acetate=3:1 as eluent to give an white colloidal solid. (1.12 g, 79% yield).

Workup

  1. customTo a 100 mL sealed tube
  2. temperatureAfter cooling to rt
  3. extractionthe water phase was extracted with ethyl acetate (3×30 mL)
  4. washwashed with brine (3×30 mL)
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product was purified with an silica gel chromatography with hexane/ethyl acetate=3:1 as eluent
  8. customto give an white colloidal solid

Sources & evidence

ORD record
ord-65b5d8210a1249ec9ba2cb1fceeb1b0b
Source dataset
uspto-grants-2016_08
Patent number
US09425415B2

Reaction notes

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