Pyridine → [5-(1-Methoxy-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]carbamic acid 2,2,2-trichloro-ethyl ester

Temperature

-15 °C

To an ice-salt cooled solution of 5-(1-methoxy-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (Preparation 11, 2.43 g, 10 mmol) and pyridine (0.9 mL, 11 mmol) in THF (30 mL), add a solution of 2,2,2-trichloroethylchloroformate (2.12 g, 10 mmol) in THF (10 mL) dropwise. Stir at −15° C. for 0.5 hour, then at 22° C. for 1 hour. Partition the reaction mixture between dichloromethane (50 mL) and saturated aq. sodium bicarbonate (50 mL). Isolate the aqueous phase and extract twice with dichloromethane (25 mL each). Dry the combined organic phases over sodium sulfate and concentrate. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to give a white solid (3.73 g, 89% yield, ES+(m/z) 418.1 [M+H]).

1. waitat 22° C. for 1 hour
2. customPartition the reaction mixture between dichloromethane (50 mL) and saturated aq. sodium bicarbonate (50 mL)
3. customIsolate the aqueous phase
4. extractionextract twice with dichloromethane (25 mL each)
5. dry with materialDry the combined organic phases over sodium sulfate
6. concentrationconcentrate
7. washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate
8. customto give a white solid (3.73 g, 89% yield, ES+(m/z) 418.1 [M+H])

ORD record

ord-1c0f4660d90c4e9a8523e9f28272863a

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582638B2