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Lithium Chloride → 2-(2-methylallyl)-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbonitrile

HRID 1773933
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773933
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)[C:3]=1[C:24]#[N:25].[CH2:26]([Sn](CCCC)(CCCC)CCCC)[C:27](=[CH2:29])[CH3:28].[K].[Li+].[Cl-]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][C:27](=[CH2:26])[CH2:29][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)[C:3]=1[C:24]#[N:25]
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Komponenten

6

Edukt 3

HCID 433294Lithium ChlorideHCID 867039962-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbonitrileHCID 86704025Potassium methallyltributyltin

Produkt 1

HCID 867040242-(2-methylallyl)-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbonitrile (example 221) (107 mg, 0.239 mmole) in DMF (4 mL) are added potassium methallyltributyltin (331 mg, 0.95 mmole), Pd(PPh3)4 (28 mg, 0.025 mmole), LiCl (51 mg, 1.30 mmole). The flask is evacuated and filled with argon. The reaction mixture is heated at 110° C. for 5 hours. AcOEt and water are added, as well as a 10% KF solution. The aqueous phase is extracted with AcOEt. The organic phase is washed with 0.5N HCl. The HCl phase is made alkaline with 1H NaOH and the aqueous phase is extracted with AcOEt. The organic phase is dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH) (100:0) to (95:5) to give 2-(2-methylallyl)-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbonitrile.

Aufarbeitung

  1. customThe flask is evacuated
  2. additionfilled with argon
  3. additionAcOEt and water are added
  4. extractionThe aqueous phase is extracted with AcOEt
  5. washThe organic phase is washed with 0.5N HCl
  6. extractionthe aqueous phase is extracted with AcOEt
  7. dry with materialThe organic phase is dried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customThe residue is purified by silica gel chromatography
  11. washeluting with (CH2Cl2:MeOH) (100:0) to (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-c7aa1789845246888c5f997da2cc3bf9
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255101B2

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