Acetonitrile → 4-chloro-6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1878613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878613
Br[C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.[CH3:12][C:13]#[N:14]>CC1C=CC=C([Sn](CCCC)(CCCC)CCCC)N=1.C(OCC)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>[Cl:11][C:4]1[CH:3]=[C:2]([C:13]2[CH:12]=[CH:2][CH:3]=[C:4]([CH3:5])[N:14]=2)[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]=12

Komponenten

6

Edukt 2

HCID 6342AcetonitrileHCID 247295876-Bromo-4-chloro-1H-pyrrolo[2,3-B]pyridine

Produkt 1

HCID 687902414-chloro-6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 114631832-Methyl-6-(tributylstannyl)pyridineLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (1 eq, 11.0 mmol, 2.76 g) in MeCN (20 ml), 2-methyl-6-tributylstannanyl-pyridine (see Chemistry, A European Journal (2005), 11 (23), 6818-6828) (1 eq, 11.0 mmol, 4.19 g) and Pd(PPh3)4 (0.01 eq, 0.110 mmol, 131 mg) are added. The resulting mixture is heated using microwave radiation for 15 min at 160° C. The mixture is diluted with diethyl ether and extracted with aqueous HCl solution (2 M). The aqueous layer is basified with aqueous NaOH solution (4 M) and extracted with DCM. The organic layer is dried with MgSO4, filtered, and concentrated. The residue is taken up in hexane and stirred at r.t. for 1 h. The suspension is filtered and dried giving the title compound; [M+H]+=244.

Aufarbeitung

  1. temperatureThe resulting mixture is heated
  2. customfor 15 min
  3. customat 160° C
  4. extractionextracted with aqueous HCl solution (2 M)
  5. extractionextracted with DCM
  6. dry with materialThe organic layer is dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe suspension is filtered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fe753493e87047c18640a683fc65b60f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314112B2

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