4-BROMOPYRIDINE-2-CARBALDEHYDE

4-bromo-N-methoxy-N-methylpicolinamide (42; 5.84 g, 23.8 mmol) was dissolved in anhydrous THF (100 ml) and cooled to -78° C and 1.0 M lithium aluminum hydride in THF (14.3 ml, 14.3 mmol) was added via syringe and then the resulting mixture was stirred for 1 hour. 1 M NaOH (20 ml) and water (20 ml) was added carefully to the reaction mixture, and then the resulting solution was stirred for 30 minutes. Ethyl acetate and water was added, the organic phase was washed with water and brine, dried over NaExample 29i Under the protection of nitrogen, Add 3L DCM to the 5L three-neck bottle to cool down.240g of oxalyl chloride was added dropwise during cooling;At -60 ° C, 295.6 g of Dimethyl sulfoxide (DMSO) was added dropwise to the reaction solution.Keep warm for 30min;At -60 ° C, 237.5 g of Cpd 3 was added dropwise to the reaction solution.The reaction was carried out at -65 ° C for 1 hour;At this temperature, 3.5 eq of triethylamine (TEA) was added dropwise.After the solution was allowed to stand, the plate was measured.Through the column, the product 4-bromopyridine-2-carbaldehyde is obtained.(Cpd 4) 177.2g, The yield was 75percent.[0505] Step 2: Synthesis of 4-bromo-2-(1, 3-dioxolan-2-yl)pyridine. To a stirred solution of 4- bromopicolinaldehyde in toluene was added ethylene glycol 4- bromo-2-(1, 3-dioxolan-2-yl)pyridine 1H-NMR (400 MHz, CDCh: delta (ppm): 8.43 (d, J=5.2 Hz, 1H), 7.72 (d, J=2 Hz, 1H), 7.47-7.45 (dd, J=2 Hz, lH), 5.83 (s, lH), 4.18-4.06 (m, 4H).

Molecular Weight:186.01
XLogP3:1.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:184.94763
Monoisotopic Mass:184.94763
Topological Polar Surface Area:30
Heavy Atom Count:9
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes