Pyridine → HCID 68808135, compound

Temperature

0 °C

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (4 g, 18.6 mmol) was dissolved in 200 mL dry diethyl ether under Ar, cooled in an ice water bath, added dry pyridine (9 mL, 111 mmol) followed by the dropwise addition of oxalyl chloride (4.8 mL, 54 mmol). A precipitate forms immediately. The reaction was stirred vigorously at 0° C. for one hour, 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 (2 g, 8.5 mmol) oil in 40 mL dry DCM under Ar, cooled to 0° C., added 2.8 mL pyridine followed by 4-bromo-2-trifluoromethylaniline (2.05 g, 8.6 mmol). The reaction was allowed to warm to ambient temperature, stirred overnight then concentrated. Redissolved in 100 mL EtOAc, washed with 1 N HCl (3×50 mL), brine (100 mL), dried with MgSO4, filtered and concentrated to yield title compound. (1.98 g, 53%) APCI (AP−): 435.0, 437.0 (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. temperaturecooled to 0° C.
7. temperatureto warm to ambient temperature
8. stirringstirred overnight
9. concentrationthen concentrated
10. dissolutionRedissolved in 100 mL EtOAc
11. washwashed with 1 N HCl (3×50 mL), brine (100 mL)
12. dry with materialdried with MgSO4
13. filtrationfiltered
14. concentrationconcentrated

ORD record

ord-f763a25f18ef43478b2f5b48684f5ec6

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07407972B2