2-BOC-AMINOMETHYL-PHENYLBORONIC ACID PINACOL ESTER

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Palladium(II) acetate (35.0 mg, 0.156 mmol) and Xantphos (90 mg, 0.156 mmol) was added to degassed THF (3 ml) and let stir for 5 minutes then transferred to a separate rxn vessel that contained tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (1142 mg, 3.43 mmol), 2,4-diiodooxazole (1000 mg, 3.12 mmol), Potassium phosphate (1985 mg, 9.35 mmol) and degassed Tetrahydrofuran (THF) (12 mL). The rxn vessel was capped and heated to 80° for 16 hours. Filtered and the residue was purified via Biotage (0% to 100% DCM:Hex; 50 g-HP-silica gel column) to obtain 460 mg of tert-butyl 2-(2-iodooxazol-4-yl)benzylcarbamate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (s, 9H) 4.39 (d, J=5.31 Hz, 2H) 5.40 (br. s., 1H) 7.31-7.45 (m, 2H) 7.53 (dd, J=19.45, 7.07 Hz, 2H) 7.94 (s, 1H); MS[MH]+=401.1 to degassed THF (3 ml) then transferred to a separate rxn vessel degassed Tetrahydrofuran (THF) (12 mL) The rxn vessel was capped heated to 80° for 16 hours Filtered the residue was purified via Biotage (0% to 100% DCM:Hex; 50 g-HP-silica gel column)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Palladium(II) acetate (35.0 mg, 0.156 mmol) and Xantphos (90 mg, 0.156 mmol) was added to degassed THF (3 ml) and let stir for 5 minutes then transferred to a separate rxn vessel that contained tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (1142 mg, 3.43 mmol), 2,4-diiodooxazole (1000 mg, 3.12 mmol), Potassium phosphate (1985 mg, 9.35 mmol) and degassed Tetrahydrofuran (THF) (12 mL). The rxn vessel was capped and heated to 80° for 16 hours. Filtered and the residue was purified via Biotage (0% to 100% DCM:Hex; 50 g-HP-silica gel column) to obtain 460 mg of tert-butyl 2-(2-iodooxazol-4-yl)benzylcarbamate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (s, 9H) 4.39 (d, J=5.31 Hz, 2H) 5.40 (br. s., 1H) 7.31-7.45 (m, 2H) 7.53 (dd, J=19.45, 7.07 Hz, 2H) 7.94 (s, 1H); MS[MH]+=401.1 to degassed THF (3 ml) then transferred to a separate rxn vessel degassed Tetrahydrofuran (THF) (12 mL) The rxn vessel was capped heated to 80° for 16 hours Filtered the residue was purified via Biotage (0% to 100% DCM:Hex; 50 g-HP-silica gel column)