Carbazole → HCID 86710448, compound

HRID 2168844Notes

Reaction equation

HRID 2168844 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH:11]1[C:23]2[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1>O1CCOCC1.[Cu]I.NCC(N)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([N:22]2[C:23]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:16]3[C:21]2=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:7]=1

Participants

6

Reactant 2

HCID 6854CarbazoleHCID 1362922-Bromo-4-fluoroanisole

Product 1

HCID 86710448HCID 86710448, compoundYield 260.9%

Reagents, catalysts & solvents 3

HCID 6567PropylenediamineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-4-fluoroanisole (20 g, 10 mmol, 1 equiv) and carbazole (18.4 g, 11 mmol, 1.1 equiv) were dissolved in 1,4-dioxane (200 mL). Potassium phosphate tribasic hydrate (46 g, 20 mmol, 2 equiv), copper(I) iodide (1 g, 0.5 mmol, 0.05 equiv) and 1,2-diaminopropane (1 mL, 1.3 mmol, 0.13 equiv) were added and the reaction was refluxed for 18 hours. The reaction was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure and the residue was purified over silica gel (250 g), eluting with gradient of 0 to 10% ethyl acetate in heptanes to give compound 4 (7.6 g, 26% yield) as an off white solid that was contaminated with carbazole. This material was used subsequently.

Workup

  1. temperaturethe reaction was refluxed for 18 hours
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified over silica gel (250 g)
  5. washeluting with gradient of 0 to 10% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-ea1a3f5fe95445e6a8f14551caa5efaa
Source dataset
uspto-grants-2015_06
Patent number
US09045568B2

Reaction notes

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