Reaction #70281

Reaction equation

tert-butyl 2-amino-5-methylbenzoate

2-bromo-5-iodopyridine

BINAP

NaOtBu

→

expected product

Yield 40.2%

tert-Butyl 2-(6-bromopyridin-3-ylamino)-5-methylbenzoate

Yield 40.2%

Solvents

ethyl acetate

Water

toluene

Conditions

Workup

1. 1
   ExtractionThe aqueous phase was extracted again with more ethyl acetate
2. 2
   WashThe organic phase was washed with water and brine
3. 3
   Otherdried
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude mixture was purified by chromatography (Biotage 40S, SiO2, Hexane:Ethyl acetate from 0% to 10%)

Procedure

In a schlenck tube, a mixture of tert-butyl 2-amino-5-methylbenzoate (2.89 mmol, 0.600 g), 2-bromo-5-iodopyridine (2.89 mmol, 0.822 g), BINAP (0.29 mmol, 0.096 g), Pd2(dba)3 (0.14 mmol, 0.132 g) and NaOtBu (5.79 mmol, 0.556 g) in toluene (15 ml) was heated at 120° C. for 3 hours. Water and ethyl acetate were added to the reaction crude. The aqueous phase was extracted again with more ethyl acetate. The organic phase was washed with water and brine, dried, filtered and concentrated in vacuo. The crude mixture was purified by chromatography (Biotage 40S, SiO2, Hexane:Ethyl acetate from 0% to 10%) affording 0.422 g (yield 40%) of the expected product.

Source