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Potassium Carbonate → 5-(5-chloropyridazin-3-yl)-1-methyl-1H-indazole

HRID 879396
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 879396
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15](B(O)O)=[CH:16][CH:17]=2)[CH:12]=[N:11]1.C([O-])([O-])=O.[K+].[K+]>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>[Cl:8][C:6]1[CH:7]=[C:2]([C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[N:10]([CH3:9])[N:11]=[CH:12]3)[N:3]=[N:4][CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 199596873,5-DichloropyridazineHCID 225589101-Methyl-1H-indazole-5-boronic acid

Produkt 1

HCID 867002035-(5-chloropyridazin-3-yl)-1-methyl-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

3,5-dichloropyridazine (200 mg, 1.34 mmol), 1-methyl-1H-indazole-5-boronic acid (260 mg, 1.48 mmol), K2CO3 (556.6 mg, 4.03 mmol), and tetrakis(triphenylphosphine)palladium(0) (233, 0.20 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed 1,4-dioxane (10 mL) and degassed water (2.5 mL). The reaction mixture was heated at 95° C. for 2 h then cooled to room temperature. The reaction mixture was filtered through Celite (ethyl acetate eluent) and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+: calc'd for C14H10ClN4: 245.1 (M+H+); Found: 245.2 (M+H+). 1H NMR (400 MHz, Chloroform-d) δ 9.15 (d, J=2.2 Hz, 1H), 8.44 (s, 1H), 8.21 (dd, J=8.8, 1.5 Hz, 1H), 8.11 (s, 1H), 7.97 (s, 1H), 7.56 (d, J=8.8 Hz, 1H), 4.14 (s, 3H).

Aufarbeitung

  1. customflushed with argon three times
  2. additionTo this mixture was added
  3. customdegassed 1,4-dioxane (10 mL)
  4. customdegassed water (2.5 mL)
  5. temperaturethen cooled to room temperature
  6. filtrationThe reaction mixture was filtered through Celite (ethyl acetate eluent)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
  9. customprovided the product

Quellen und Nachweise

ORD-Eintrag
ord-93210446a980437181a609f7022fb7f9
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987250B2

Notizen zur Reaktion

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