Reaktion #1572127

Reaktionsgleichung

5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-tert-butylthiophene-2-sulfonamide

(Z)-tributyl(prop-1-enyl)stannane

→

(Z)—N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(prop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide

Ausbeute 82.1%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas flushed with nitrogen
2. 2
   workup.ADDITIONAnhydrous dioxane (10 mL) was added
3. 3
   Sonstigethe reaction mixture was flushed with nitrogen
4. 4
   ExtraktionThe mixture was extracted with EtOAc
5. 5
   Waschenwashed with water, brine
6. 6
   EinengenThe organic layers were concentrated
7. 7
   Sonstigeto afford the residue, which
8. 8
   Sonstigewas purified by silica gel chromatography (PE/EA/MeOH=2:1:0.06 as eluant)

Vorschrift

A mixture of 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-tert-butylthiophene-2-sulfonamide (497.4 mg, 1.0 mmol, 1.0 eq), Pd(PPh3)2Cl2 (28.0 mg, 0.1 mmol, 0.1 eq) and Bu4NBr (321.1 mg, 0.1 mmol, 1.0 equiv.) was flushed with nitrogen. Anhydrous dioxane (10 mL) was added and the reaction mixture was flushed with nitrogen. (Z)-tributyl(prop-1-enyl)stannane (475.4 mg, 1.5 mmol, 1.5 eq) was added and the reaction mixture was stirred at rt for 2 h. The mixture was extracted with EtOAc and washed with water, brine. The organic layers were concentrated to afford the residue, which was purified by silica gel chromatography (PE/EA/MeOH=2:1:0.06 as eluant) to afford (Z)—N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(prop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide (375.6 mg, 82.1%) as white solid. LC-MS (m/z)=459 [M+H]+.

Quelle