3-Iodobenzoyl chloride → HCID 66987381, compound
Reaction equation
[Mg].Br[C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[C:5]([O:13][CH3:14])[CH:4]=1.[I:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20]>>[I:15][C:16]1[CH:17]=[C:18]([C:19]([C:3]2[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[C:5]([O:13][CH3:14])[CH:4]=2)=[O:20])[CH:22]=[CH:23][CH:24]=1Participants
Procedure
First, magnesium was added to 1-bromo-3,4,5-trimethoxybenzene as a starting material, as shown in Reaction 6, and then 3-iodobenzoyl chloride was added thereto to obtain a Compound 21 derivative [(3-iodophenyl)(3,4,5-trimethoxyphenyl)methanone]. Thus obtained compound (88 mg, 0.250 mmol) was dissolved in tetrahydrofuran (2.5 ml), and 2-(tributylstannyl)thiazole (135 μl, 0.425 mmol) and Pd(PPh3)2Cl2 (8.79 mg, 0.012 mmol) were slowly added thereto at room temperature. The mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was diluted with EtOAc, and an aqueous sodium bicarbonate solution was added thereto. An organic layer was extracted out from the resulting solution. The organic layer was washed with water, and brine, and dried over anhydrous MgSO4. The solid substance was filtered off, and the filtrate was vacuum concentrated. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=2/1→1/1) to obtain Compound 581 (20 mg, 22%) in a form of a yellow solid.
Workup
- customas shown in Reaction 6
Sources & evidence
- ORD record
- ord-e92387434a8245fda31696b309360f97
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053439B2
Reaction notes
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