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

HRID 1766427Notes

Reaction equation

HRID 1766427 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]3[C:20](=[O:26])[N:21]([CH:23]([CH3:25])[CH3:24])[CH2:22][C:9]=23)=[CH:4][CH:3]=1.I[CH3:28]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]3[C:20](=[O:26])[N:21]([CH:23]([CH3:24])[CH3:25])[CH:22]([CH3:28])[C:9]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 218687853-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one

Product 1

HCID 114409623-(4-Chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-4-methyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-oneYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-137b5e583d2546938b623da741461334
Source dataset
uspto-grants-2007_06
Patent number
US07230024B2

Reaction notes

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