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To a solution of <strong>[90721-35-0]8-amino-5-bromoisoquinoline</strong> in 48percent HBF4 (3OmL) at 0 0C was slowly added an aqueous (1OmL) solution of NaNO2 (172mg, 2.5mmol). The reaction mixture was stirred at 0 0C for Ih and was then concentrated under reduced pressure to give a dark residue. The dark residue was heated to 150 0C for 16h. The resulting dark oil was cooled to 23 0C, quenched with ammonium hydroxide and extracted with DCM. The organic solution was concentrated and the resulting dark solid was recrystallized from EtOAc/Hexanes. The desired product (lOOmg) was in the mother liquor while the by-product was filtered away as a solid. LCMS showed an m/z of 228.0/226.0 with a retention time of 1.318min, method [I].
With n-butyllithium; isopropylamine; DavePhos;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 0 - 23℃; for 16h;
A 3OmL reaction vial was flame dried and charged with isopropylamine (0.67mL, 4.8mmol) in toluene (3mL). The solution was chilled to 0 0C before a 1.5M solution of nBuLi (4.8mmol, 3.2mL) was added. Pd2(dba)3 catalyst (184mg, 0.2mmol) was added, followed by ligand 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (160mg, 0.4mmol), and t-butylacetate (464mg, 4mmol). After 15min, a toluene (3mL) solution of 5- bromo-8-fluoroisoquinoline (200mg, 0.9mmol) was added. The reaction was stirred for 16h while warming to 23 0C. The crude mixture was purified by column chromatography (3percent MeOH/DCM) to give tert-butyl 2-(8-fluoroisoquinolin-5-yl)acetate (140mg). LCMS showed an m/z of 262.1 with a retention time of 1.469min, method [I].
N-(4-fluorophenyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide[ No CAS ]
[ 679433-94-4 ]
2‐[4‐(8‐fluoroisoquinolin‐5‐yl)phenyl]‐N‐(4‐fluorophenyl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
59%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In 1,4-dioxane; at 100℃; for 6h;
Compound 17 (30 mg, 0.085 mmol),<strong>[679433-94-4]5-bromo-8-fluoroisoquinoline</strong> (19 mg, 0.085 mmol),Pd[PPh3]4 (10mg, 0.0085mmol)And CsF (38 mg, 0.255 mmol) was heated to 100 C in dioxane (2 mL) for 6 hours.Concentrated and added water (100 mL), EtOAc (EtOAc)The organic phase was separated and dried over anhydrous Na 2 SO 4Filter and concentrate, and the residue was purified by silica gel column chromatography.Elution with ethyl acetate/petroleum ether (2:3) gave the desired compound I-43 (19 mg, 59%).