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Trimethylaluminum (23.9 mL, 47.8 mmol, 2M sol. in toluene) was added to a vigorously stirred solution of 7-chloro-1 H-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1.38 g, 1.19 mmol) in THF (109 mL) under argon. The reaction mixture was stirred at 65C for 16 h. The mixture was cooled to RT and poured into sat. aq. NH4CI. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3x). The combined organic extracts were washed with brine then dried (Phase separator) and concentrated under reduced pressure to give 7-methyl-1 H- pyrazolo[3,4-c]pyridine as a solid. MS (LC-MS): 134 [M+H]+, tR (HPLC conditions k): 0.25 min.
With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; toluene; at 65℃; for 16.0h;Inert atmosphere;
Trimethylaluminum (23.9 ml_, 47.8 mmol, 2M in toluene) was added to a vigorously stirred solution of 7-chloro-1 H-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1 .38 g, 1.19 mmol) in THF (109 ml.) under argon. The reaction mixture was stirred at 65C for 16 h. The mixture was cooled to RT and poured into sat. aq. NH4CI. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under reduced pressure to give 7-methyl-1 H-pyrazolo[3,4- c]pyridine as a solid. MS (LC-MS): 134 [M+H]+; tR (HPLC conditions d): 0.25 min.
With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; toluene; at 65℃; for 16.0h;Inert atmosphere;
Trimethylaluminum (23.9 mL, 47.8 mmol, 2M sol. in toluene) was added to a vigorously stirred solution of <strong>[76006-11-6]7-chloro-1H-pyrazolo[3,4-c]pyridine</strong> (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1.38 g, 1.19 mmol) in THF (109 mL) under argon. The reaction mixture was stirred at 65C for 16 h, cooled to RT and poured into sat. aq. NH4CI. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3x). The combined organic extracts were washed with brine then dried (phase separator) and concentrated to give 7-methyl-i H-pyrazolo[3,4-c]pyridine as a solid. MS (LC/MS): 134 [M+H]+, tR (H PLC conditions d): 0.25 mm.
With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; toluene; at 65℃; for 16.0h;Inert atmosphere;
Trimethylaluminum (23.9 mL, 47.8 mmol, 2M sol. in toluene) was added to a vigorously stirred solution of 7-chloro-iH-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1.38 g, 1.19 mmol) in THF (109 mL) under argon. The reaction mixture was stirred at 65C for 16 h, cooled to RT and poured into sat. aq. NH4CI solution. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3x). The combined organic extracts were washed with brine then dried (phase separator) and concentrated to give 7-methyl-i H-pyrazolo[3,4-c]pyridine as a solid. MS (LC/MS): 134 [M+H]+, tR (HPLC conditions d): 0.25 mm.
(4S,6S)-4-(5-((2-(difluoromethyl)-2H-pyrazolo[3,4-c]pyridin-7-yl)amino)-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine 2,2,2-trifluoroacetate[ No CAS ]
With caesium carbonate; In hexane; ethyl acetate; N,N-dimethyl-formamide;
Step 2: 7-chloro-2-(difluoromethyl)-2H-pyrazolo[3,4-c]pyridine A mixture of <strong>[76006-11-6]7-chloro-1H-pyrazolo[3,4-c]pyridine</strong> (4.99 g, 32.5 mmol), sodium chlorodifluoroacetate (14.86 g, 97 mmol), and cesium carbonate (40.2 g, 123 mmol) in DMF (81 ml) was heated at 95 C. for 4 h. The reaction was allowed to cool to rt and the solids were filtered. The filtrate was diluted with water and extracted with EtOAc. The organic extract was washed with water, satd NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (100 g), eluting with a gradient of 5% to 60% EtOAc in hexane, to provide a white solid (1.4117 g, 6.93 mmol, 21.34% yield). MS m/z=203.9 [M+H]+. Calculated for C7H4ClF2N3: 203.
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