Reacción #970457

Ecuación de reacción

(S)-6-(Isopropyl(methyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate

1,3,5-trimethyl-1H-pyrazole-4-boronic acid pinacol ester

K2CO3

→

desired product

Rendimiento 56.0%

(2S)-Isopropyl-methyl-[5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amine

Rendimiento 56.0%

Disolventes

1,2-dimethoxyethane

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was purged with Ar (g) for 10 min
2. 2
   Temperaturawarmed up
3. 3
   Temperaturato reflux
4. 4
   Otroto reach room temperature
5. 5
   workup.ADDITIONdiluted with CH2Cl2 (20 mL)
6. 6
   ExtracciónIt was extracted with CH2Cl2 (3×20 mL)
7. 7
   Secadothe organic layer was dried over anhydrous Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated
10. 10
    OtroThe obtained crude
11. 11
    Otrowas purified by flash chromatography on silica gel (5% Et3N/AcOEt)

Procedimiento

(S)-6-(Isopropyl(methyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate (184 mg, 0.524 mmol), 1,3,5-trimethyl-1H-pyrazole-4-boronic acid pinacol ester (142 mg, 0.602 mmol) and Pd(PPh3)4 (60 g, 0.0524 mmol) were added to a solution of K2CO3 (145 mg, 1.047 mmol) in a mixture of 1,2-dimethoxyethane (7 mL) and H2O (1 mL). The reaction mixture was purged with Ar (g) for 10 min, and warmed up to reflux. The reaction was completed in 4 h. It was allowed to reach room temperature, diluted with CH2Cl2 (20 mL) and acidified with HCl aqueous solution (10%, 30 mL). The organic layer was discarded, and the aqueous layer was taken to pH=9-10 with NaOH aqueous solution (10%). It was extracted with CH2Cl2 (3×20 mL), and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude was purified by flash chromatography on silica gel (5% Et3N/AcOEt), to afford 91 mg of the desired product (yellow oil, 56% yield).

Fuente