Reaction #62070

Reaction equation

[6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-thianthren-2-yl]-carbamic acid tert-butyl ester

2-chloro-6-morpholin-4-yl-pyran-4-one

2-Chloro-6-morpholin-4-yl-pyran-4-one

K2CO3

→

title compound

Yield 127.4%

[6-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-thianthren-2-yl]-carbamic acid tert-butyl ester

Yield 127.4%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   workup.ADDITIONwas then added The dark brown mixture
2. 2
   ConcentrationThe reaction mixture was concentrated in vacuo and water (100 ml)
3. 3
   workup.ADDITIONwas added
4. 4
   FiltrationThe brown solid was filtered
5. 5
   Washwashed with water
6. 6
   Otherdried overnight in a vacuum desiccator
7. 7
   Otherwas used without any further purification

Procedure

[6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-thianthren-2-yl]-carbamic acid tert-butyl ester (8.34 g, 18.24 mmol), 2-chloro-6-morpholin-4-yl-pyran-4-one (3)(4.72 g, 21.89 mmol) and grinded K2CO3 (5.04 g, 36.48 mmol) were dissolved in dry 1,4-dioxane (100 ml). The mixture was degassed for 15 minutess and Pd(PPh3)4 (1.02 g, 0.91 mmol) was then added The dark brown mixture was heated to 100° C. under an atmosphere of N2 for 24 hour. The reaction mixture was concentrated in vacuo and water (100 ml) was added. The brown solid was filtered, washed with water, dried overnight in a vacuum desiccator and was used without any further purification to give the title compound (11.87 g). m/z (LC-MS, ESP), RT=4.61 min, (M++1)=511.2

Source