1,2-Diaminocyclohexane → 9-(9-Tosyl-carbazol-3-yl)-pyrido[2,3-b]indole

HRID 2039427Notes

Reaction equation

HRID 2039427 reaction equation
[S:1]([N:11]1[C:23]2[CH:22]=[CH:21][C:20](I)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N:25]1[C:30]2[NH:31][C:32]3[C:37]([C:29]=2[CH:28]=[CH:27][CH:26]=1)=[CH:36][CH:35]=[CH:34][CH:33]=3.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(N)CCCCC1N>[Cu]I.C1(C)C=CC=C(C)C=1>[S:1]([N:11]1[C:23]2[CH:22]=[CH:21][C:20]([N:31]3[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:29]4[CH:28]=[CH:27][CH:26]=[N:25][C:30]3=4)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

7

Reactant 4

HCID 46101,2-DiaminocyclohexaneHCID 62657Potassium Phosphate, TribasicHCID 674869H-Pyrido(2,3-b)indoleHCID 66974690N-tosyl-3-iodocarbazole2×

Product 1

HCID 708152249-(9-Tosyl-carbazol-3-yl)-pyrido[2,3-b]indole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7929M-XyleneSolvent

Procedure

The synthesis of N-tosyl-3-iodocarbazole is described in WO2009/086028. Into a 250 mL flask was added 9H-pyrido[2,3-b]indole (5 g, 29.7 mmol), N-tosyl-3-iodocarbazole (14.63 g, 32.7 mmol), copper(I) iodide (0.283 g, 1.486 mmol) and potassium phosphate (13.25 g, 62.4 mmol). It was degassed before the addition of anhydrous m-xylene (150 mL) and cyclohexane-1,2-diamine (0.339 g, 2.97 mmol). The resultant green suspension was refluxed for three days. Column chromatography on silica gel (eluent hexane/DCM 1:4, v/v) provided the product 9-(9-tosyl-carbazol-3-yl)-pyrido[2,3-b]indole (9.9 g).

Workup

  1. temperatureThe resultant green suspension was refluxed for three days

Sources & evidence

ORD record
ord-834e106a02774db4b6daf837a13c0321
Source dataset
uspto-grants-2013_11
Patent number
US08580399B2

Reaction notes

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