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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 857490
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 857490
[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
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Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-262ecc0ebc404cb39aa3cbfcaad5706a
Quelldatensatz
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07145012B2

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