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Hydrogen Peroxide → 6-Hydroxy-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796603
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1796603
OO.B(F)(F)F.CC[O:9]CC.OC([C:16]1[C:17]([CH3:41])=[C:18]2[C:23]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)=[C:22]([C:38]#[N:39])[CH:21]=[N:20][N:19]2[CH:40]=1)(C)C>C(Cl)Cl>[OH:9][C:16]1[C:17]([CH3:41])=[C:18]2[C:23]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:29][CH:30]=3)=[C:22]([C:38]#[N:39])[CH:21]=[N:20][N:19]2[CH:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 221796836-(1-Hydroxy-1-methyl-ethyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

Produkt 1

HCID 221796716-Hydroxy-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a mixture of H2O2 (50% wt in H2O, 0.0115 mL, 0.20 mmol) and CH2Cl2 (2 mL) at −5° C. was added BF3.OEt2. The reaction was stirred at −5° C. for 40 min before a solution of compound 145 (56 mg, 0.14 mmol) in CH2Cl2 (3 mL) was added. The reaction was kept at −5° C. for 10 min and quenched with an aqueous solution of Na2SO3 (2 g, 10 mL). The reaction was diluted with CH2Cl2 and the two layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The CH2Cl2 layers were combined and concentrated in vacuo to give a brown oil. This crude oil was purified by silica gel flash chromatography (eluted with 10% EtOAc/CH2Cl2) to give compound 146 as a yellow solid (32 mg, 64%). HPLC: 90% at 1.89 min (retention time) (Phenom-Prime S5 C18 column, 4.6×30 mm, eluting with 10-90% aqueous methanol over 2 min containing 0.1% TFA, 5 mL/min, monitoring at 220 nm). MS (ES): m/z 357 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. customquenched with an aqueous solution of Na2SO3 (2 g, 10 mL)
  3. additionThe reaction was diluted with CH2Cl2
  4. customthe two layers were separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil
  8. customThis crude oil was purified by silica gel flash chromatography (eluted with 10% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3c8d783f5e0447888e1aefa3a2c5cb02
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07030112B2

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