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Cesium carbonate → 4-tert-butyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridine-1-yl-phenyl)-benzenesulfonamide

HRID 75985
Notes
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Reaction equation

HRID 75985 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2I)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[N:31][C:26]=2[N:25]=[N:24]1.C([O-])([O-])=O.[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:23]2[C:27]3[C:26](=[N:31][CH:30]=[CH:29][CH:28]=3)[N:25]=[N:24]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 594281524-tert-butyl-N-(4-chloro-2-iodo-phenyl)-benzenesulfonamideHCID 178420751HCID 178420751, compound

Product 1

HCID 251349214-tert-butyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridine-1-yl-phenyl)-benzenesulfonamide

Reagents, catalysts & solvents

2
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A 4 mL scintillation vial was charged with 4-tert-butyl-N-(4-chloro-2-iodo-phenyl)-benzenesulfonamide (84 mg, 0.19 mmol), 4-azabenzotriazole (29 mg, 0.22 mmol), CuI (3 mg, 0.014 mmol), Cs2CO3 (127 mg, 0.39 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (5 mg, 0.04 mmol), and dioxane (500 μL). The reaction was heated to 90° C. and stirred overnight. The following day, the volatiles were removed in vacuo. The residue was subsequently diluted in EtOAc and washed with saturated NH4Cl (aq). The organic layer was then concentrated in vacuo and the residue purified by preparative TLC (thin-layer chromatography) to afford 4-tert-butyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridine-1-yl-phenyl)-benzenesulfonamide: MS (ES) M+H expected 442.1, found 442.0.

Workup

  1. customThe following day, the volatiles were removed in vacuo
  2. additionThe residue was subsequently diluted in EtOAc
  3. washwashed with saturated NH4Cl (aq)
  4. concentrationThe organic layer was then concentrated in vacuo
  5. customthe residue purified by preparative TLC (thin-layer chromatography)

Sources & evidence

ORD record
ord-cafa98523a5c4f5ca92a5b8d549abfd2
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835468B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes