4-(2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline → HCID 67347550, Verbindung

HRID 1676374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676374
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[S:19][C:18]4[C:13](=[N:14][CH:15]=[CH:16][C:17]=4[O:20][C:21]4[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=4[F:28])[CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[S:19][C:18]4[C:13](=[N:14][CH:15]=[CH:16][C:17]=4[O:20][C:21]4[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=4[F:28])[CH:12]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Komponenten

5

Edukt 2

HCID 673482014-(2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroanilineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67347550HCID 67347550, VerbindungAusbeute 25,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A round-bottomed flask was charged with 4-(2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline (Example 161, Step A, 50.0 mg, 0.125 mmol), palladium on carbon (44.6 mg, 0.0376 mmol, 10%) and MeOH (10 mL). The air was exchanged with nitrogen three times and then was exchanged with hydrogen another three times. Then the reaction mixture was stirred under hydrogen at room temperature until the starting material had been consumed (overnight). The mixture was filtrated to remove the palladium on carbon and then the solvent was removed under reduced pressure to afford crude product. The crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (12.8 mg, 25.5%). LRMS (APCI pos): m/e 401 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.40 (m, 1H), 7.25 (s, 1H), 7.02 (t, 1H), 6.42-6.60 (m, 3H), 4.00 (s, 4H), 3.81 (br s, 2H), 2.89 (m, 1H), 2.14 (m, 2H), 1.90 (m, 4H), 1.72 (m, 2H).

Aufarbeitung

  1. customhad been consumed (overnight)
  2. filtrationThe mixture was filtrated
  3. customto remove the palladium on carbon
  4. customthe solvent was removed under reduced pressure
  5. customto afford crude product
  6. customThe crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1

Quellen und Nachweise

ORD-Eintrag
ord-7f26115229e14b5db46af9aff0d746f3
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003662B2

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