Ethyl Acetate → 6-Pyridin-4-yl-4-(3-vinyl-1H-indol-2-yl)-2H-pyridazin-3-one

HRID 1786699Notes

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[C:12](=[O:23])[NH:13][N:14]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:16]=1.[CH2:24]([Sn](CCCC)(CCCC)C=C)[CH2:25]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>[N:20]1[CH:21]=[CH:22][C:17]([C:15]2[CH:16]=[C:11]([C:3]3[NH:4][C:5]4[C:10]([C:2]=3[CH:24]=[CH2:25])=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:12](=[O:23])[NH:13][N:14]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 104 mg 4-(3-Iodo-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one (example 25), 123 mg tributyl(vinyl)tin, 41 mg tetraethylammonium-chloride and 9 mg bis(triphenylphosphine)palladium(II) chloride in DMF is stirred at 80° C. for 40 min. After cooling to room temperature, 4 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 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

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

Sources & evidence

ORD record: ord-4c08ebff04e74637bf2cec2accec9dc6
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507734B2

Reaction notes

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