Potassium Carbonate → 3-Chloro-N-[2-(4-isoquinolinyl)-3,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide

HRID 573655

Reaktionsgleichung

Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[CH3:23].[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](B(O)O)=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:27]4[C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:24]=[N:25][CH:26]=4)=[C:3]([CH3:23])[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 77) (100 mg, 0.232 mmol) in 1,4-dioxane (2 mL) and water (1 mL) was added 4-isoquinolinylboronic acid (40.1 mg, 0.232 mmol), bis(triphenylphosphine)palladium(II) chloride (16.26 mg, 0.023 mmol) and potassium carbonate (112 mg, 0.811 mmol) and the mixture heated at 100° C. for 1 h using a microwave reactor. The mixture was then filtered through celite, washing with ethyl acetate (30 mL) and the filtrate evaporated to dryness. The residue was then purified by MDAP (acidic conditions), to afford the title compound (41.45 mg). LCMS (A) m/z: 480 [M+1]+, Rt 1.13 min (acidic).

Aufarbeitung

filtrationThe mixture was then filtered through celite
washwashing with ethyl acetate (30 mL)
customthe filtrate evaporated to dryness
customThe residue was then purified by MDAP (acidic conditions)

Quellen und Nachweise

ORD-Eintrag: ord-df96f4948d40466e8266fbf0709b341c
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09029545B2

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