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Sodium Hydroxide → 9-(9H-carbazol-3-yl)-pyrido[2,3-b]indole

HRID 2039428
Notes
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Reaction equation

HRID 2039428 reaction equation
S([N:11]1[C:23]2[CH:22]=[CH:21][C:20]([N:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26]4[CH:33]=[CH:34][CH:35]=[N:36][C:25]3=4)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>C1COCC1.C(O)C.O>[CH:22]1[C:23]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[C:20]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]3[CH:33]=[CH:34][CH:35]=[N:36][C:25]2=3)[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 708152249-(9-Tosyl-carbazol-3-yl)-pyrido[2,3-b]indole

Product 1

HCID 708151019-(9H-carbazol-3-yl)-pyrido[2,3-b]indoleYield 70.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture solution of 9-(9-tosyl-carbazol-3-yl)-pyrido[2,3-b]indole (9.9 g, 20.30 mmol) and NaOH (8.12 g, 203 mmol) in THF (100 mL), ethanol (50 mL) and water (50 mL) was refluxed over weekend. After cooling to room temperature, the white solid was obtained by filtration, and washed successively with water, ethanol, DCM and ethanol to yield the 9-(9H-carbazol-3-yl)-9H-pyrido[2,3-b]indole (4.8 g).

Workup

  1. customthe white solid was obtained by filtration
  2. washwashed successively with water, ethanol, DCM and ethanol

Sources & evidence

ORD record
ord-efa52f0cb2d54664bb821b23f7a559bf
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580399B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes