Cesium carbonate → 2-[1-(Cyclopropylmethyl)-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl]-6-fluorobenzonitrile

온도

100 °C

To a microwave vial was added 1-(cyclopropylmethyl)-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (2-1) (0.043 g, 0.12 mmol), 2-bromo-6-fluorobenzonitrile (0.035 g, 0.18 mmol), cesium carbonate (0.077 g, 0.24 mmol), palladium bis(tri-tert-butylphosphine) (0.012 g, 0.024 mmol), dioxane (1 mL), and water (0.2 mL). The reaction mixture was then heated under microwave irradiation at 100° C. for 10 minutes. The crude reaction mixture was then allowed to cool to room temperature, diluted with methanol, then filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) to give 2-[1-(cyclopropylmethyl)-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl]-6-fluorobenzonitrile (2-2) as a white solid. HRMS (M+H)+: observed=358.1015, calculated=358.1020

1. customThe crude reaction mixture
2. temperatureto cool to room temperature
3. filtrationfiltered
4. concentrationconcentrated
5. customPurification of crude
6. customreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water)

ORD 기록

ord-b9ea5e157821412aa2139a9acc37b357

출처 데이터셋

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09108937B2