Pyridine → HCID 68807807, compound

Temperature

0 °C

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1.97 g, 9.2 mmol) was dissolved in 150 mL dry diethyl ether under Ar, cooled in an ice water bath, added dry pyridine (3.7 mL, 45.8 mmol) followed by the dropwise addition of oxalyl chloride (2 mL, 22.9 mmol). A precipitate forms immediately. The reaction was stirred vigorously at 0° C. for 2 hours, then at ambient temperature for one hour. Added 100 mL diethyl ether, filtered off solids washing with diethyl ether. Concentrated the filtrates to an off-white oil. Redissolved oil in 100 mL dry DCM under Ar, cooled to 0° C., added 3 mL pyridine followed by 2-amino-5-bromopyridine (1.32 g, 7.6 mmol). The reaction was allowed to warm to ambient temperature, stirred for 3 hours then concentrated. Redissolved in 250 mL EtOAc, washed with 10% HCl (3×100 mL), brine (100 mL), dried with MgSO4, filtered and concentrated to yield title compound as a yellow sticky solid. (2.74 g, 97%) APCI (AP−): 368.0, 370.0 (M−H)−.

1. temperaturecooled in an ice water bath
2. waitat ambient temperature for one hour
3. filtrationfiltered off solids
4. washwashing with diethyl ether
5. concentrationConcentrated the filtrates to an off-white oil
6. dissolutionRedissolved oil in 100 mL dry DCM under Ar
7. temperaturecooled to 0° C.
8. additionadded 3 mL pyridine
9. temperatureto warm to ambient temperature
10. stirringstirred for 3 hours
11. concentrationthen concentrated
12. dissolutionRedissolved in 250 mL EtOAc
13. washwashed with 10% HCl (3×100 mL), brine (100 mL)
14. dry with materialdried with MgSO4
15. filtrationfiltered
16. concentrationconcentrated

ORD record

ord-83763489e1ef454fba3c250d5255b2f0

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07407972B2