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With copper(l) iodide; bis(tri-t-butylphosphine)palladium(0); tetrabutylammomium bromide; potassium acetate; In N,N-dimethyl-formamide; at 160℃; for 0.25h;Microwave irradiation; Inert atmosphere; Sealed tube;
Step 7: Intermediate 4016E (100 mg, 0.195 mmol) is charged in a microwave vial and dissolved in DMF (4.0 ml_). Intermediate 4016F (28 mg, 0.23 mmol, 1 .2 eq), potassium acetate (38 mg, 0.39 mmol, 2.0 eq), tetra-butylammonium bromide (63 mg, 0.20 mmol, 1 .0 eq) and copper (I) iodide (74 mg, 0.39 mmol, 2 eq) are added and the reaction mixture is degassed with argon. Bis(tri-t-butylphosphine)palladium (0) (10 mg, 0.020 mmol, 0.10 eq) is added and the vial is sealed and warmed in a microwave oven at 160 C for 15 min. The reaction mixture is concentrated and the residue is purified by flash chromatography (10% MeOH in DCM) and by preparative HPLC to provide compound 4016 (tR: 1 .67, (M+H)+: 552.4).
With acetic acid; at 160℃; for 0.5h;Microwave irradiation;
A mixture of 3-aminopyridin-4-ol (500 mg, 4.54 mmol), trimethoxymethane (5 mL), and acetic acid (0.4 mL) was irradiated with microwave radiation for 0.5 h at 160 C. The resulting mixture was concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 : 10 ethyl acetate/petroleum ether) to afford oxazolo[4,5-c]pyridine (0.23 g, 42%) as a yellow solid. MS: (ESI, m/z ): 121 [M+H]+.
With acetic acid; at 160℃; for 0.5h;Microwave irradiation; Sealed tube;
Step 6: 3-Amino-4-hydroxypyridine (Fluorochem) (500 mg, 4.54 mmol) is charged in a microwave vial and suspended in trimethylorthoformate (5.0 ml_). AcOH (0.400 ml.) is added and vial is sealed and warmed in a microwave oven at 160 C for 30 min. The reaction mixture is concentrated and the residue is purified by flash chromatography (50% EtOAc in hexanes to 100% EtOAc) to provide intermediate 4016F.
methyl 1,1-dimethyl-2,3-dihydro-1H-isoindole-4-carboxylate[ No CAS ]
methyl (E)-2-(((4-hydroxypyridin-3-yl)imino)methyl)-1,1-dimethylisoindoline-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
37%
With trifluorormethanesulfonic acid; In acetonitrile; at 60℃;
A solution of <strong>[273-56-3]oxazolo[4,5-c]pyridine</strong> (100 mg, 0.83 mmol), methyl 1,1 -dimethyl-2, 3- dihydro-lH-isoindole-4-carboxylate (340 mg, 1.66 mmol), and trifluoromethanesulfonic acid (12.5 mg, 0.083 mmol) in CH3CN (8 mL) was stirred overnight at 60 C in an oil bath. The resulting mixture was concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10-20% methanol-dichloromethane) to afford methyl (E)-2-(((4-hydroxypyridin-3-yl)imino)methyl)-l, l-dimethylisoindoline-4-carboxylate (100 mg, 37%) as a white solid. MS: (ESI, m/z): 326 [M+H]+.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
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