Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[CH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])[CH:8]=2)[CH:3]=[CH:2]1.B(OB=O)=O.[Br:23][C:24]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:25]=1[CH:26]=O.B(OCCCC)(OCCCC)OCCCC.C(N)CCC.Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[Br:23][C:24]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:25]=1/[CH:26]=[CH:15]/[C:14](=[O:16])[CH2:13][C:12](=[O:17])/[CH:11]=[CH:10]/[C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Procedure
6-(1H-Indol-6-yl)hex-5-ene-2,4-dione (19.4 mg, 85 μmol) and boron trioxide (11 mg, 0.16 mmol) was placed in a 20 mL reaction vessel, and dissolved in 0.4 mL of ethyl acetate. To the stirring mixture at 80° C. was added a solution of 2-bromo-5-hydroxybenzaldehyde (23 mg, 0.11 mmol) and tri-n-butyl borate (25 μL, 93 μmol), sequentially. After the reaction mixture was stirred for 2 h at the same temperature, n-butylamine (10 μL, 0.10 mmol) was added with additional stirring for 1 h. The reaction mixture was treated with a 1:1 solution (1 mL) of 1N HCl and brine at room temperature, and was stirred at 50° C. for 5 min to 1 h (if necessary, the reaction mixture was neutralized by saturated NaHCO3 aqueous solution). The organic layer was purified directly by silica gel column chromatography (eluting with hexane/ethyl acetate or chloroform/methanol) to obtain the title compound (7.0 mg, 19%) as a solid.
Workup
- additionwas added
- stirringwas stirred at 50° C. for 5 min to 1 h (if necessary, the reaction mixture
- customThe organic layer was purified directly by silica gel column chromatography (eluting with hexane/ethyl acetate or chloroform/methanol)
Sources & evidence
- ORD record
- ord-0de48525a50d43d8988a55d51e46a549
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552220B2
Linked notes
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