Synthetic Route of 1060812-84-1 ,Some common heterocyclic compound, 1060812-84-1, molecular formula is C7H5BrN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
A solution mixture of 5-bromopyrazolo[1 ,5-a]pyridine 94-2 (900 mg, 4.59 mmol) and tBuONa (661 .2 mg, 6.88 mmol) in toluene (10 mL) was degassed with argon for about 10 mm. To this mixture were added Pd2(dba)3 (84 mg, 0.091 mmol), BINAP (114.2 mg, 0.lO2mmol) and cyclopropylamine (2 mL, 28.87 mmol) under argon atmosphere. The resulting reaction mixture was maintained at 90C for 2 h under microwave irradiation. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was washed with water (30 mL), brine (25 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography over silica-gel (100-200 mesh) using a solvent gradient of 25% ethyl acetate in pet-ether to afford 500 mg (62%) of N-cyclopropylpyrazolo[1,5-a]pyridin-5- amine 147-1 as a brown solid. 1H-NMR (400 MHz, CDCI3): c58.18 (d, J= 7.5 Hz, 1H), 7.78 (d, J= 2.2 Hz, 1H), 6.72 (d, J= 2.6 Hz, 1H), 6.15-6.18 (m, 2H), 4.28 (5, 1H), 2.44-2.49 (m, 1 H), 0.78-0.80 (m, 2H), 0.54-0.58 (m, 1 H). ESI-LC/MS: m/z 173.75 (M+H); R =1 .99 mm [Waters Acquity UPLC with Quattro-micro detector; Waters Acquity BEH Cl 8,1.7 pm, 2.1 X 50 mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) hold for 0.5 mm and to 10:90 H20 (0.025% TEA):CH3CN (0.025% TEA) in 3.5 mm and hold for 1 .5 mm with flow rate of 0.4 mLlmin].
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060812-84-1, its application will become more common.
Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; KONDREDDI, Ravinder Reddy; LEONG, Seh Yong; MISHRA, Pranab Kumar; MOREAU, Robert Joseph; ROLAND, Jason Thomas; SIM, Wei Lin Sandra; SIMON, Oliver; TAN, Liying Jocelyn; YEUNG, Bryan KS; ZOU, Bin; BOLLU, Venkatataiah; WO2014/78802; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem