Reaction #1583899

Reaction equation

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide

toluene

potassium carbonate

EtOH

4-methylphenylboronic acid

→

4′-methybiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide

Solvents

EtOAc

water

water

Conditions

Workup

1. 1
   Temperatureheated at 70° C. for 30 minutes
2. 2
   TemperatureThe mixture was then cooled to room temperature
3. 3
   WashThe mixture was washed with saturated aqueous NaCl
4. 4
   Extractionextracted with EtOAc
5. 5
   Dryingdried over MgSO4
6. 6
   Filtrationfiltered through Celite®
7. 7
   Concentrationconcentrated
8. 8
   Otherto yield the crude product as a red solid (8.6 g)
9. 9
   OtherThe solid material was triturated with 1:1 EtOAc
10. 10
    Filtrationhexanes, filtered
11. 11
    Washrinsed with hexanes
12. 12
    Otherto yield the crude product as a reddish-brown solid (6.2 g)
13. 13
    OtherThe solid material was again triturated with EtOAc
14. 14
    Filtrationfiltered
15. 15
    Washrinsed with EtOAc

Procedure

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide (5.36 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol), potassium carbonate (5.1 g, 36.8 mmol), water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol) were combined and the mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was then added. The mixture was heated at 60° C. for about 2 hours, then heated at 70° C. for 30 minutes. The mixture was then cooled to room temperature and water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered through Celite® and concentrated to yield the crude product as a red solid (8.6 g). The solid material was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield the crude product as a reddish-brown solid (6.2 g). The solid material was again triturated with EtOAc, filtered, and rinsed with EtOAc to yield 4′-methybiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide as a light brown solid (4.6 g; 96.2% purity).

Source