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Ethyl Acetate → 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-vinyl-1H-indole

HRID 2234077
Notes
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Reaction equation

HRID 2234077 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:14]=[N:13][C:12]=1[O:23][CH3:24].[CH2:25]([Sn](CCCC)(CCCC)C=C)[CH2:26]CC.[F-].[K+].CCOC(C)=O>[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:24][O:23][C:12]1[N:13]=[N:14][C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:16][C:11]=1[C:3]1[NH:4][C:5]2[C:10]([C:2]=1[CH:25]=[CH2:26])=[CH:9][CH:8]=[CH:7][CH:6]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 522689Potassium FluorideHCID 231029143-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole

Product 1

HCID 230925092-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-vinyl-1H-indole

Reagents, catalysts & solvents 3

HCID 5946
Tetraethylammonium Chloride
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 430 mg 3-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole, 490 mg tributyl(vinyl)tin, 165 mg tetraethylammonium-chloride and 35 mg bis(triphenylphosphine)palladium(II) chloride in DMF is stirred at 80° C. for 40 min. After cooling to room temperature, 15 ml aqueous potassium fluoride solution (30%) are added and the mixture stirred for 30 min at room temperature before extraction with EtOAc. The organic layer is dried over MgSO4 and the solvent evaporated ion prior to purification of the crude product by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% HCOOH).

Workup

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe organic layer is dried over MgSO4
  3. customthe solvent evaporated ion
  4. customto purification of the crude product by preparative RP-HPLC
  5. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% HCOOH)

Sources & evidence

ORD record
ord-61e7c4e3c5674bd895217371c6e2f765
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709466B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes