Reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:11][CH:10]=2)O1.C(OC(=O)[C:32]1[CH:37]=[CH:36][C:35](I)=[CH:34][CH:33]=1)C.[C:40]([O-:43])([O-])=[O:41].[Na+].[Na+].O.CO[CH2:49][CH2:50]OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:49]([O:43][C:40]([C:11]1[CH:10]=[CH:9][C:14]([C:36]2[CH:37]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:13][C:12]=1[C:15]1[S:16][CH:17]=[CH:18][C:19]=1[NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:22])=[O:23])=[O:41])[CH3:50]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Heat in a sealed tube with stirring propane-2-sulfonic acid{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide (0.5 mmol), 4-iodo-benzoic acid ethyl ester (0.75 mmol), 2M Na2CO3 water solution (0.2 mL) and Pd(PPh3)4 (0.05 mmol) in 4.0 ml of an anhydrous DME to 100° C. for 24 h. Evaporate the organic solvent, prior to the addition of water (10 mL). Extract the mixture with dichloromethane (3×20 mL) and dry the combined organic phases (Na2SO4) and concentrate to furnish a crude mixture. Purification by flash chromatography (Silica gel-hexane/EtOAc) yields the title compound.
Workup
- customEvaporate the organic solvent
- additionto the addition of water (10 mL)
- extractionExtract the mixture with dichloromethane (3×20 mL)
- dry with materialdry the combined organic phases (Na2SO4)
- concentrationconcentrate
- customto furnish a crude mixture
- customPurification by flash chromatography (Silica gel-hexane/EtOAc)
Sources & evidence
- ORD record
- ord-5b7048ec6a9c44d197a51e5820c4c004
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393868B2
Linked notes
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