Ammonium Chloride → 5,7-dimethyl-1H-pyrazolo[3,4-c]pyridine
Reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:11])[CH:5]=[C:6]2[CH:10]=[N:9][NH:8][C:7]=12.[CH3:12][Al](C)C.[NH4+].[Cl-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C:4]1[CH:5]=[C:6]2[CH:10]=[N:9][NH:8][C:7]2=[C:2]([CH3:12])[N:3]=1Participants
Conditions
- Temperature
- 65 °C
Procedure
To a vigorously stirred solution of 7-bromo-5-methyl-1H-pyrazolo[3,4-c]pyridine (3.65 g, 14.6 mmol) and Pd(PPh3)4 (845 mg, 0.73 mmol) in THF (65 mL) was added trimethylaluminum (14.6 mL, 29.3 mmol; 2 M sol. in toluene) under argon. The reaction mixture was stirred at 65° C. for 60 h, and then was cooled to RT and poured into a sat. aq. NH4Cl solution. The resulting suspension was filtered, the solid was washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3×). The combined organics were washed with brine, then dried (Phase separator) and concentrated under reduced pressure to give 5,7-dimethyl-1H-pyrazolo[3,4-c]pyridine as a solid. MS (LC-MS): 148 [M+H]+, tR (HPLC conditions k): 0.50 min.
Workup
- temperaturewas cooled to RT
- filtrationThe resulting suspension was filtered
- washthe solid was washed with water
- extractionThe filtrate and the combined washings were extracted with EtOAc (3×)
- washThe combined organics were washed with brine
- customdried (Phase separator)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0411f260596045d087619d14a0e591b5
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085555B2
Reaction notes
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