Iodine → HCID 59133922, compound

Temperature

-45 °C

To a solution of methyl 1-(1-methylethyl)-3-methyl-1H-pyrazole-4-carboxylate (2.00 g, 11.0 mmol) in dry tetrahydrofuran (22.0 mL) at −78° C., 2 M solution of butyllithium (6.04 mL, 12.1 mmol) in pentane was added dropwise. The reaction mixture was then warmed to −45° C. and stirred for 1 h. It was then cooled to −78° C. and a solution of iodine (3.06 g, 12.1 mmol) in THF (11.0 mL) was added. The reaction mixture was warmed to RT and stirred for 1 h. Then it was quenched with saturated NH4Cl solution and extracted with ethyl acetate (2×25 mL). The organic layers were combined, washed with brine and dried (MgSO4). Evaporation of solvent gave a tan solid as title compound (3.38 g, 11.0 mmol, 100% crude yield). MS m/z 309 (MH+); 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 1.41 (d, 6H) 2.47 (s, 3H) 3.82 (s, 3H) 4.77 (m, 1H).

1. temperatureIt was then cooled to −78° C.
2. temperatureThe reaction mixture was warmed to RT
3. stirringstirred for 1 h
4. customThen it was quenched with saturated NH4Cl solution
5. extractionextracted with ethyl acetate (2×25 mL)
6. washwashed with brine
7. dry with materialdried (MgSO4)
8. customEvaporation of solvent

ORD record

ord-5684a659ebc54af2b5643b571b8b811c

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652004B2