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Water → 4-(1-methylpiperidin-4-yloxy)-2-p-tolyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

HRID 1773861
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773861
I[C:2]1[N:11]=[C:10]2[N:4]([CH2:5][CH2:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH:9]2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:3]=1.O.[CH3:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[CH3:19][N:16]1[CH2:17][CH2:18][CH:13]([O:12][CH:9]2[C:8]3[CH:20]=[CH:21][CH:22]=[CH:23][C:7]=3[CH2:6][CH2:5][N:4]3[C:10]2=[N:11][C:2]([C:29]2[CH:30]=[CH:31][C:26]([CH3:25])=[CH:27][CH:28]=2)=[CH:3]3)[CH2:14][CH2:15]1
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Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 726957782-iodo-4-(1-methyl piperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Produkt 1

HCID 867039484-(1-methylpiperidin-4-yloxy)-2-p-tolyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysator
HCID 152416121,1`-Bis(diphenylphosphino)ferroceneKatalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 2) (50 mg, 0.12 mmole) in 1,4-dioxane (0.5 mL) are added water (0.1 mL), 4-methylbenzeneboronic acid (25 mg, 0.18 mmole), Pd(OAc)2 (1.4 mg, 6 μmmole), 1,1-bis(diphenylphosphino)ferrocene (3.3 mg, 6 μmmole) and K2CO3 (50 mg, 0.36 mmole). The vial is evacuated and filled with argon. The reaction mixture is stirred at 100° C. for 3.5 hours. Water is added to the reaction mixture, and the pH is adjusted to 9-10 by adding saturated Na2CO3 solution. The aqueous phase is extracted three times with AcOEt. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (99:5:0.1) to (95:5:0.5). The residue is purified by preparative TLC eluting with (CH2Cl2:MeOH:NH4OH) (9:9:0.1) to give 4-(1-methylpiperidin-4-yloxy)-2-p-tolyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

Aufarbeitung

  1. customThe vial is evacuated
  2. additionfilled with argon
  3. additionWater is added to the reaction mixture
  4. additionby adding saturated Na2CO3 solution
  5. extractionThe aqueous phase is extracted three times with AcOEt
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure
  9. customThe residue is pre-purified by silica gel chromatography
  10. customThe residue is purified by preparative TLC
  11. washeluting with (CH2Cl2:MeOH:NH4OH) (9:9:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-425e076ded39491e89b87be12cafc526
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255101B2

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