Sodium Carbonate → 4-chloro-1,6-dimethyl-3-(3-(pyrrolidin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

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Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([CH3:13])[CH:10]=[C:11](I)[C:3]=12.[N:14]1([C:19]2[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.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.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([CH3:13])[CH:10]=[C:11]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)[CH:20]=3)[C:3]=12

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A mixture of 4-chloro-3-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine (D13) (500 mg, 1.631 mmol), (3-(pyrrolidin-1-yl)phenyl)boronic acid (374 mg, 1.957 mmol), bis(triphenylphosphine)palladium(II) chloride (114 mg, 0.163 mmol) and sodium carbonate (2M aq. solution) (8 mL, 16.00 mmol) was heated at 65° C. for 1 hour. The mixture was transferred to a separatory funnel with ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (30 mL×3). The organics were combined, dried over magnesium sulfate and concentrated. The crude was purified over normal phase chromatography eluting with ethyl acetate and cyclohexane (0-30%) to give the title compound (135 mg). LCMS (A): m/z (M+H)+ 326, C19H20ClN3 requires 325 (acidic).

Aufarbeitung

extractionThe aqueous layer was extracted with ethyl acetate (30 mL×3)
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe crude was purified over normal phase chromatography
washeluting with ethyl acetate and cyclohexane (0-30%)

Quellen und Nachweise

ORD-Eintrag: ord-31c5eb6fd12745bca93f3d1e53bd2432
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08877742B2

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