反応 #1572127

反応方程式

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

収率 82.1%

反応条件

後処理

1. 1
   その他was flushed with nitrogen
2. 2
   workup.ADDITIONAnhydrous dioxane (10 mL) was added
3. 3
   その他the reaction mixture was flushed with nitrogen
4. 4
   抽出The mixture was extracted with EtOAc
5. 5
   洗浄washed with water, brine
6. 6
   濃縮The organic layers were concentrated
7. 7
   その他to afford the residue, which
8. 8
   その他was purified by silica gel chromatography (PE/EA/MeOH=2:1:0.06 as eluant)

実験手順

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]+.

出典