Cesium carbonate → N-[3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-benzyl]-methanesulfonamide

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Reaktionsgleichung

Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([I:10])[N:4]2[N:3]=1.[CH3:11][S:12]([NH:15][CH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)(=[O:14])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>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.O>[I:10][C:9]1[N:4]2[C:5]([S:6][C:2]([C:21]3[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=3)[CH2:16][NH:15][S:12]([CH3:11])(=[O:14])=[O:13])=[N:3]2)=[N:7][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.25 g, 0.757 mmol, 1 eq), (3-methanesulfonylaminomethylphenyl)boronic acid (0.208 g, 0.908 mmol, 1.2 eq), cesium carbonate (0.493 g, 1.514 mmol, 2 eq), Pd(PPh3)2Cl2 (0.053 g, 0.075 mmol, 0.1 eq), 1,4-dioxane (6 mL) and water (6 mL) was heated in a pressure tube at 115° C. for 4 h. Solvents were removed and the slurry obtained was partitioned between water and 10% MeOH in DCM. The organic layer was dried, filtered and evaporated. The residue was purified in an Isolute Flash Si II column (EtOAc) to give the desired product (77 mg, 23%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.04 min, [M+H]+ m/z 435.0.

Aufarbeitung

customSolvents were removed
customthe slurry obtained
customwas partitioned between water and 10% MeOH in DCM
customThe organic layer was dried
filtrationfiltered
customevaporated
customThe residue was purified in an Isolute Flash Si II column (EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-fef5e99258494a0eb5c6768bb0db94ca
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08815918B2

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