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5-(4,4,5,5-Tetramethyl[1,3,2]-dioxaborolan-2-yl)-2,3-dihydro-benzofuran The title compound, MS: m/e=246.1 (M') was obtained as a light yellow oil (51% yield) using 2,3-dihydro-5-iodobenzo[b]furan.
2
[ 937591-69-0 ]
(S)-1-(4-iodophenyl)ethyl diisopropylcarbamate[ No CAS ]
(R)-2-(1-(benzofuran-5-yl)-1-(4-iodophenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane[ No CAS ]
7-chloro-5-(2,3-dihydro-1-benzofuran-5-yl)quinoxaline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
17%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 1.0h;Inert atmosphere; Sealed tube;
A pressure vessel is charged with 5-bromo-7-chloro-quinoxaline (Intermediate 2 (288 mg, 1 .18 mmol, 1 eq.), 5-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-2,3-dihydrobenzofuran (306 mg; 1.18 mmol; 1 eq.), cesium carbonate (779 mg; 2.37 mmol; 2 eq.), 1 ,2-dimethoxyethane (10 mL) and water (5 mL). The reaction mixture is sparged with argon under sonication before Pd(dppf)Cl2*CH2CI2 (148 mg; 0.18 mmol; 0.15 eq.) is added. The tube is sealed and the reaction mixture is stirred at 100 C for 1 h. After coming back to room temperature, the reaction mixture is partitioned between EtOAc and water. The aq. layer is extracted with EtOAc and the combined organic layers are washed with water and brine, dried over Na2S04 filtered through a pad of celite and concentrated in vacuo. Purification of the residue by FCC (EtOAc gradient in hexane) affords 7- chloro-5-(2,3-dihydro-1-benzofuran-5-yl)quinoxaline (58 mg; 0.20 mmol; yield: 17%; off-white powder; UPLC purity: 97%)
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