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Ethyl Acetate → 5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-nicotinic acid ethyl ester

HRID 1171106
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1171106
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[C:10](B(O)O)[CH:11]=1)=[O:5])[CH3:2].Br[C:16]1[CH:17]=[C:18]2[C:24](I)=[N:23][N:22]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:19]2=[N:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:40]([O:43][CH2:44][CH3:45])(=O)C>O>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[C:10]([C:16]2[CH:17]=[C:18]3[C:24]([C:10]4[CH:11]=[CH:6][CH:4]=[CH:45][C:44]=4[O:43][CH3:40])=[N:23][N:22]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:19]3=[N:20][CH:21]=2)[CH:9]=[N:8][CH:7]=1)[CH3:2]
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Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 55265795(5-(Ethoxycarbonyl)pyridin-3-yl)boronic acidHCID 598361345-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 598360525-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-nicotinic acid ethyl ester
Ausbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-ethoxycarbonyl-5-pyridylboronic acid (529 mg, 1.91 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (66 mg, 0.09 mmol) and 5-bromo-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (780 mg, 1.80 mmol) acetonitrile (5 mL) and 2 M aqueous solution of sodium carbonate (5 mL) were added and the mixture was irradiated in a Personal Chemistry Optimizer to 90° C. for 30 minutes. The crude reaction mixture was distributed between ethyl acetate and water. The aqueous phase was extracted three times with ethyl acetate and the combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-nicotinic acid ethyl ester (552 mg, 61% yield) as a yellow oil. 1H-NMR (500 MHz, d6-DMSO) δ 9.24 (d, 1H), 9.12 (d, 1H), 9.03 (d, 1H), 8.60 (t, 1H), 8.56 (d, 1H), 7.66 (dd, 1H), 7.51 (ddd, 1H), 7.25 (dd, 1H), 7.12 (dt, 1H), 5.88 (s, 2H), 4.40 (q, 2H), 3.87 (s, 3H), 3.71 (t, 2H), 1.37 (t, 3H), 0.87 (t, 2H), −0.073 (t, 9H). MS: m/z 505 [MH+].

Aufarbeitung

  1. additionwere added
  2. customthe mixture was irradiated in a Personal Chemistry Optimizer to 90° C. for 30 minutes
  3. customThe crude reaction mixture
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aab8bad668f346e9b870b6e1d5668ef1
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07829558B2

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