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1,2-Diaminocyclohexane, trans- → 9-(dibenzo[b,d]thiophen-4-yl)-3-fluoro-9H-carbazole

HRID 879914
Notes
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Reaction equation

HRID 879914 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.I[C:16]1[C:21]2[S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:20]=2[CH:19]=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu]I.O1CCOCC1>[CH:19]1[C:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[S:22][C:21]=2[C:16]([N:6]2[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 4583534-IododibenzothiopheneHCID 158868413-Fluorocarbazole

Product 1

HCID 867225089-(dibenzo[b,d]thiophen-4-yl)-3-fluoro-9H-carbazoleYield 48.1%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 6.7 g (36.2 mmole) 3-fluoro-9H-carbazole, 11.2 g (36.2 mmole) of 4-iododibenzo[b,d]thiophene, 17.1 g (90 mmole) of copper(I) iodide, 19.1 g (90 mmole) of potassium phosphate, 10.3 g (90 mmole) of trans-1,2-cyclohexanediamine and 1,4-dioxane 700 ml were refluxed under nitrogen for about overnight. Then, the solution was filtered at 110° C. To receive the filtrate, And the 1,4-dioxane was removed under reduced pressure from the filtrate. The filtrate was extracted with 500 ml dichloromethane and 2000 ml water, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-ethyl acetate) to give product 6.4 g (48%).

Workup

  1. temperaturewere refluxed under nitrogen for about overnight
  2. filtrationThen, the solution was filtered at 110° C
  3. customthe 1,4-dioxane was removed under reduced pressure from the filtrate
  4. extractionThe filtrate was extracted with 500 ml dichloromethane and 2000 ml water
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c71573ea9d664314be50bf5f1de4d2dd
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993130B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes