Reaktion #79307

Reaktionsgleichung

tert-butyl(6bR,10aS)-5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate

2,3-dichlorophenylboronic acid

Na2CO3

→

tert-butyl(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole carboxylate

Ausbeute 159.2%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was degassed one more time
2. 2
   TemperaturThe reaction mixture was refluxed for 15 h
3. 3
   workup.ADDITIONThe reaction mixture was diluted with EtOAc
4. 4
   Waschenwashed with saturated NaHCO3 and brine
5. 5
   TrocknenThe combined organic layer was dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was chromatographed (silica gel; Hexane:EtOAc 3:1)

Vorschrift

A solution of tert-butyl(6bR,10aS)-5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate (150 mg, 0.37 mmol) and 2,3-dichlorophenylboronic acid (143 mg, 0.75 mmol) in benzene (10 mL) and 2M Na2CO3 aqueous solution (0.74 mL, 1.48 mmol) was degassed at 20° C. Pd(PPh3)2Cl2 (7.8 mg, 0.01 mmol) was added, and the reaction mixture was degassed one more time. The reaction mixture was refluxed for 15 h then cooled to 20° C. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 and brine. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed (silica gel; Hexane:EtOAc 3:1) to give tert-butyl(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole carboxylate as a light yellow solid (140 mg, 81%).

Quelle