TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE

A solution of 4-bromopyridin-2-amine (519 mg) in dry THF (15 mL) was treated with bis(trimethylsilyl)-amide (1 M in hexane, 6 mL) at −5° C. and the solution was stirred at this temperature for 10 minutes. Di-tert-butyl dicarbonate (654 mg) was added and the mixture was stirred at rt for 1 h. Saturated ammonium chloride solution (20 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried and the volatiles were removed under reduced pressure to yield the desired compound (96percent yield).Intermediate 20b) A solution of 4-bromopyridin-2-amine (519 mg) in dry THF (15 mL) was treated with bis(trimethylsilyl)- amide (1 M in hexane, 6 mL) at -5 °C and the solution was stirred at this temperature for 10 minutes. Di- ferf-butyl dicarbonate (654 mg) was added and the mixture was stirred at rt for 1 h. Saturated ammonium chloride solution (20 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried and the volatiles were removed under reduced pressure to yield the desired compound (96percent yield).fe/f-butyl (4-bromopyridin-2-yl)carbamate (i5): To a stirred solution of 4-bromopyridin-2-amine (1 g, 5.7 mmol) in n-butanol (15 ml_), boc- anhydride (1 .7 ml_, 6.9 mmol) was added and the reaction was heated at 50°C for 16h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed under reduced pressure to obtain a residue. The residue was dissolved in ethyl acetate and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford fe/f-butyl (4-bromopyridin-2-yl)carbamate (i5) (1 .4 g, Yield 89percent). MS (ESI) m/e (M+1 )A 250 mL round bottom flask was added 4-bromo-2-amine (4-bromopyridin-2-amine) (5g, 28.90mmol), tert-butyl dicarbonate ((Boc)To a mixture of 4-bromo-pyridin-2-ylamine (2 g, 11.6 mmol), TEA (3.51 g, 34.8 mmol) and DMAP (100 mg) in THF (25 mL) was added BocD) TEA (311 uL; 2.23 mmol) was added to a mixture of 4-bromo-picolinic acid (450 mg; 2.23 mmol) in toluene (6.7 mL). Diphenylphosphoryl azide (480 uL; 2.23 mmol) was added and the reaction was stirred for 30 min at RT, after which tert-butanol (427 uL; 4.46 mmol) was added. The reaction mixture was heated at 90° C. for 2 h, then was cooled to RT. The solution was diluted with EtOAc (15 mL), washed with 10percent aqueous Na

Molecular Weight:273.13
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:272.01604
Monoisotopic Mass:272.01604
Topological Polar Surface Area:51.2
Heavy Atom Count:15
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes