Reaction #90439

Reaction equation

CH2Cl2 EtOAc

5-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-one

2-iodopyridine

K2CO3

→

white solid

Yield 79.4%

5-((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-2-yl)oxazolidin-2-one

Yield 79.4%

Solvents

EtOAc

DMSO

Conditions

Workup

1. 1
   Otherwas sealed tightly in a vial and
2. 2
   TemperatureThe reaction mixture was cooled
3. 3
   Washwashed with water 5×10 mL
4. 4
   DryingThe organic layer was dried over anhydrous Na2SO4
5. 5
   Otherevaporated
6. 6
   Otherto afford the crude product, which
7. 7
   Washas elute

Procedure

A mixture of 5-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-one (0.0195 g, 0.0460 mmol), 2-iodopyridine (0.0209 g, 0.102 mmol), CuI (0.0009 g, 0.00460 mmol), and K2CO3 (0.0058 g, 0.0418 mmol) in 0.5 mL of DMSO was sealed tightly in a vial and heated at 130° C. for 12 hours. The reaction mixture was cooled and diluted with 20 mL EtOAc and washed with water 5×10 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using CH2Cl2/EtOAc as elute to afford 0.0183 g white solid as product, yield 79.4%.

Source