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Water → Ethyl 2-((3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetate

HRID 402498
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 402498
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:18]([CH3:20])=[CH:17][C:16](=[O:21])[NH:15][C:14]=3[N:13]([CH3:22])[N:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CCN(C(C)C)C(C)C.Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][C:16]([O:21][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:17][C:18]=3[CH3:20])[N:13]([CH3:22])[N:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 1363765163-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

Produkt 1

HCID 67209497Ethyl 2-((3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (1.0 g, 3.34 mmol) in DMF (5 ml) were added DIPEA (1.17 ml, 6.68 mmol) and ethyl 2-bromoacetate (0.56 ml, 5.01 mmol). After stirring at 90° C. for 1 h the mixture was cooled to rt, water was added and extracted three times with CH2Cl2. The organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography (eluent 50% hexane in EtOAc) to yield 910 mg (71%) of the title compound. [1H-NMR (DMSO-d6, 600 MHz): δ 6.71 (d, 2H), 6.61 (s, 1H), 6.57 (br s, 1H), 4.98 (s, 2H), 4.18 (q, 2H), 3.91 (s, 3H), 3.78 (s, 6H), 2.37 (s, 3H), 1.21 (t, 3H); UPLC-MS RtJ=1.21 min; [M+H]+=386.1]

Aufarbeitung

  1. temperaturewas cooled to rt
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by column chromatography (eluent 50% hexane in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6a1fd7c7724f43b3b9702c6ae39b1487
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08742106B2

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