Methyl iodide → 3-(4-Chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-4-methyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one

To a solution of 3-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one 3A-1 (19 mg, 0.05 mmol) in THF (0.5 ml) at −78° C. was added LiHMDSi (55 μl, 0.055 mmol). A deep blue-black solution was formed. The reaction mixture was stirred for 0.17 hour and then iodomethane (4.4 μl, 0.07 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 0.25 h (until a yellow color formed) and at room temperature for 2 hours, quenched with sat'd aq NH4Cl, and extracted with EtOAc. The organic solution was washed with sat'd aq NaCl, dried, and concentrated in vacuo. The residue was purified on 1 mm chromatotron plates using a 1:1 EtOAc/hexane solution to give 6A-1 as a white solid (3.2 mg, 14%); +ES MS (M+1) 400.3; 1H NMR (CDCl3): δ 7.4–7.3 (m, 4H), 7.28–7.24 (m, 2H), 7.1-7.06 (m, 2H), 4.84–4.77 (m, 1H), 4.37–4.27 (m, 1H), 1.48–1.4 (m, 9H).

1. customA deep blue-black solution was formed
2. stirringThe reaction mixture was stirred at −78° C. for 0.25 h (until a yellow color
3. customformed) and at room temperature for 2 hours
4. customquenched with sat'd aq NH4Cl
5. extractionextracted with EtOAc
6. washThe organic solution was washed with sat'd aq NaCl
7. customdried
8. concentrationconcentrated in vacuo
9. customThe residue was purified on 1 mm chromatotron plates

ORD record

ord-262ecc0ebc404cb39aa3cbfcaad5706a

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07145012B2