Acetonitrile → 6-(Pyrrolidinylcarbonyl)-3-[4-(4-methylpiperizin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1888549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888549
[N:1]1([C:6]([C:8]2[N:16]=[CH:15][C:14]3[NH:13][C:12]4[N:17]=[CH:18][C:19](Br)=[CH:20][C:11]=4[C:10]=3[CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22](#[N:24])[CH3:23]>C(=O)([O-])[O-].[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:1]1([C:6]([C:8]2[N:16]=[CH:15][C:14]3[NH:13][C:12]4[N:17]=[CH:18][C:19]([C:9]5[CH:10]=[CH:14][C:22]([N:24]6[CH2:4][CH2:5][N:1]([CH3:6])[CH2:2][CH2:3]6)=[CH:23][CH:8]=5)=[CH:20][C:11]=4[C:10]=3[CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 6342AcetonitrileHCID 582665346-(Pyrrolidinylcarbonyl)-3-bromo-9H-dipyrido[2,3-b:4',3'-d]pyrrole

Produkt 1

HCID 582665466-(Pyrrolidinylcarbonyl)-3-[4-(4-methylpiperizin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrroleAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A degassed mixture of 6-(pyrrolidinylcarbonyl)-3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (158 mg, 0.457 mmol), 4-(4-methylpiperizin-1-yl)-phenyl-1-boronic acid, pinacol ester (597 mg, 1.98 mmol), and bis(triphenylphosphine)palladium(II) chloride (69.0 mg, 99.0 μmol, 5.0 mol %) in acetonitrile (2.5 mL) and 1.0M aqueous sodium carbonate (2.5 mL)was heated under microwave irradiation at 120° C. for 10 minutes, allowed to cool, and partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate filtered and concentrated in vacuo. The resultant residue was purified by preparative HPLC (0-30% MeCN/water modified with 0.1% formic acid) to afford an off-white solid (10.0 mg, 5%). 1H NMR (DMSO-D5, 400 MHz) 12.39-12.29 (s, 1H), 9.01 (d, J=2.2 Hz, 1H), 8.88 (d, J=2.2 Hz, 31), 8.86 (s, 1H), 8.70 (s, 1H), 7.69 (d, J=8.7 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 3.78 (t, J=6.2 Hz, 2H), 3.57 (t, J=6.2 Hz, 2H), 3.25-3.18 (m, 4H), 2.47 (m, 3H), 2.24 (m, 4H), 1.87 (m, 4H). LCMS (Method D): RT=7.36 min, M+H+=441.

Aufarbeitung

  1. temperatureto cool
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by preparative HPLC (0-30% MeCN/water modified with 0.1% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-f143c453fedb4f9d808b490c54b2317e
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501765B2

Notizen zur Reaktion

Wird geladen…