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With N-ethyl-N,N-diisopropylamine; In toluene; at 120.0℃; for 16.0h;Sealed tube;
General procedure: A mixture of 6 (1.55 mmol), 2 (0.77 mmol), and i-Pr2NEt(1.55 mmol) in toluene (unless otherwise stated) (0.77 ml) was stirred at 120 C in a sealed tube for 16 h. The mixture was allowed to cool to room temperature. Purification method A: the mixture was concentrated and the residue was purified by reverse phase automatedpreparative HPLC. Purification method B: the mixture was concentrated and the residue was purified by flash column chromatography (SiO2). Purification method C: the mixture was diluted(DCM), washed (satd Na2CO3), dried (filtered through a Biotage phase separator), and concentrated. The residue was purified by reverse phase automated preparative HPLC.
8-(5-chloro-4-methylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 100.0℃; for 14.0h;Inert atmosphere;
2,5-Dichloro-4-methylpyridine (7 g, 43.2 mmol), 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (13.36 g, 43.2 mmol), and potassium carbonate (11.94 g, 86 mmol) were suspended in a mixture of DME (180 ml) and water (10 ml) under nitrogen at room temperature. Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.499 g, 0.432 mmol) was added as one portion, the reaction mixture was degassed and heated at 100 C. for 14 hours under nitrogen. The reaction mixture was then cooled down to room temperature and the organic phase was separated and filtered. Ethanol (100 ml) was added as one portion and the resulting mixture was stirred, then the white precipitate was filtered off. The remaining solution was evaporated and the residue was subjected to column chromatography on silica gel column, eluted with heptanes/DCM 1/1 (v/v), then heptanes/EtOAc 4/1 (v/v) to yield a white solid, which was combined with the white precipitate. The combined solids were recrystallized from DCM/heptanes, yielding 8-(5-chloro-4-methylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (11 g, 83% yield).
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 120.0℃; for 0.333333h;Inert atmosphere; Microwave irradiation;
General procedure: 5-bromo-2-fluorobenzonitrile (500 mg, 2.5 mmol), potassium trifluoro(vinyl)borate (402 mg, 3 mmol), l,r-bis(diphenylphosphino)fenOcene-palladium(II)di chloride dichloromethane complex (102 mg, 125 pmol) and triethylamine (253 mg, 2.5 mmol) were dispersed in 12 ml ethanol, degassed with argon and reacted in the microwave (120 C, 20 min). The mixture was then concentraed in vacuo, diluted with EtOAc, washed with water, dried over Na2SC>4, filtered and concentrated in vacuo before it was purified by silica column chromatography (50 g, EtOAc in Hept 0% to 50%). The product was obtained as a white solid (312 mg). Product confirmed by 1H-NMR
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