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1,4-Dioxane → 5-[3-(ethylsulfonyl)phenyl]-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

HRID 1642521
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1642521
I[C:2]1[C:7]2[C:8]3[C:9]([NH:15][C:6]=2[C:5](=[O:16])[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:3]=1)=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=3.[CH2:26]([S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29])[CH3:27].O1CCOCC1>C(Cl)Cl>[CH2:26]([S:28]([C:31]1[CH:36]=[C:35]([C:2]2[C:7]3[C:8]4[C:9]([NH:15][C:6]=3[C:5](=[O:16])[N:4]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:3]=2)=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=4)[CH:34]=[CH:33][CH:32]=1)(=[O:29])=[O:30])[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 164271023-Ethylsulfonylphenylboronic acidHCID 588800935-Iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8h-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

Produkt 1

HCID 588800415-[3-(ethylsulfonyl)phenyl]-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

In an appropriate microwave reaction vessel was placed, 5-iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido[4′,3′:4,5]pyrrolo [2,3-b]pyridin-8-one (8.0 g, 17.967 mmol), 3-(ethylsulfonyl)phenyl boronic acid (4.62 g, 21.562 mmol), and Tetrakis(triphenylphosphine)Pd(0) (6.23 g, 5.390 mmol). The solids were then suspended in a dioxane/saturated K2CO3 solution (40.0 mL, 4/1) and the mixture was heated in a large scale CEM microwave for 20 minutes at 150° C. The reaction mixture was diluted with DCM (400 mL), then filtered off undissolved solids. The organic layer was washed with brine (300 mL), dried with MgSO4, filtered and concentrated in vacuo affording an orange solid. The crude solid was washed with a hot ethyl acetate/hexanes solution (400 ml, 1/1) followed by a hot ethanol/DCM solution (400 mL, 4/1). The product was isolated by filtration, washed with ether and dried under vacuum affording an off-white solid. (6.83 g, 78%) 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (t, J=7.45 Hz, 3 H) 2.44 (s, 3 H) 3.20 (q, J=7.33 Hz, 2 H) 3.80 (s, 3 H) 5.37 (s, 2 H) 6.90 (d, J=8.59 Hz, 2 H) 7.16 (s, 1 H) 7.37 (d, J=8.59 Hz, 3 H) 7.75 (t, J=7.71 Hz, 1 H) 7.78-7.87 (m, 2 H) 8.03 (d, J=7.58 Hz, 1 H) 8.12 (s, 1 H) 8.43 (s, 1 H). ESI-MS: m/z 488.3 (M+H)+.

Aufarbeitung

  1. customIn an appropriate microwave reaction vessel
  2. filtrationfiltered off undissolved solids
  3. washThe organic layer was washed with brine (300 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customaffording an orange solid
  8. washThe crude solid was washed with a hot ethyl acetate/hexanes solution (400 ml, 1/1)
  9. customThe product was isolated by filtration
  10. washwashed with ether
  11. customdried under vacuum
  12. customaffording an off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-61d663d09823476c8ed7023b055bb8c1
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08119655B2

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