5-BROMOPYRIDINE-2-CARBONYL CHLORIDE

Brown solid

Oxalyl chloride (0.24 mmol) and 5 drops of N, N-dimethylformamide was added dropwise at room temperature, mixed with 5-bromo-pyrazolPiperidine carboxylic acid (0.05 mmol) in methylene chloride (80 ml). Was stirred at room temperature for 2 hours, the solvent was removed by distillation under reduced pressure to giveChloride 5.4 g (100percent).Thionyl chloride (10 ml, 137 mmol) was added to 5-bromopicolinic acid (5.00 g, 24.75 mmol). A drop of DMF was added, and the mixture was heated at 80 °C for 2 h. The excess thionyl chloride was removed to afford 5-bromopicolinoyl chloride (5.413 g, 24.55 mmol, 99 percent yield) as a pale yellow solid. An aliquot was quenched with methanol to afford methyl 5-bromopicolinate. MS (ESI, pos. ion) m/z: 216, 218 (M + 1).Thionyl chloride (10 mL, 150 mmol) was added to solid 5-bromopicolinic acid (1 .2 g, 6 mmol) at ambient temperature under N2. The resulting mixture was refluxed for 2 h and the volatiles were removed in vacuo. The crude acid chloride was dissolved in dry DCM (20 mL) and the solution was slowly added at 0 °C to a solution of 2-amino-2-methylpropan-1-01 (1.6 g, 18 mmol) in DCM (5 mL). After stirring 48 h at ambient temperature, solvents were removed in vacuo and the crude product was purified by flash chromatography on silica gel (PEIEA= 100/1 to 5/1) to the title compound (1.5 g, 93 percent) as a white solid. LCMS: [M+H] = 273.1.

Molecular Weight:220.45
XLogP3:2.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:218.90865
Monoisotopic Mass:218.90865
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes