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Potassium Carbonate → 2-[5-(2-Cyano-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide

HRID 1715642
Notes
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Reaction equation

HRID 1715642 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:7]([C:6]1[CH:9]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[N:15]=[CH:14]2)#[N:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 574187532-(1H-Indazol-5-yloxy)-5-fluorobenzonitrile

Product 1

HCID 674094872-[5-(2-Cyano-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamideYield 12%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium Iodide
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
11 °C

Procedure

To a solution of 5-fluoro-2-(1H-indazol-5-yloxy)-benzonitrile (44d) (0.200 g, 0.790 mmol) in DMF (6 mL) was added 2-chloro-N,N-dimethylacetamide (0.115 g, 0.948 mmol) and tetrabutyl ammonium iodide (0.088 g, 0.237 mmol), followed by K2CO3 (0.164 g, 1.19 mmol). The mixture was heated to 11° C. for 48 hours under N2 atmosphere. The reaction mixture was concentrated under reduced pressure and dissolved in dichloromethane. The solution was washed with 1N HCl, filtered, and chromatographed on Biotage eluting with 5% MeOH in dichloromethane to afford 0.032 g of the product (12% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in dichloromethane
  3. washThe solution was washed with 1N HCl
  4. filtrationfiltered
  5. customchromatographed on Biotage
  6. washeluting with 5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-519d2b754017405bb4d3537a87d401b2
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07799782B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes