反应详情

温度

0 °C

As shown in step 4-i of Scheme 4,5-bromo-3-(1-(2,3-difluoro-4-methoxyphenyl)-1H-tetrazol-5-yl)pyridin-2-amine (Compound 1005, 20.0 g, 7.663 mmol) in 150 mL of DCM was cooled 0° C. Boron tribromide (20.0 mL of a 1M solution in DCM, 20 mmol) was added dropwise. After the addition was complete, the reaction mixture was warmed to room temperature and stirred for 48 hours. The reaction was carefully quenched with crushed ice and extracted with EtOAc (3×200 mL). The combined organics were washed with water, washed with brine, and dried over sodium sulfate. After filtration, the volatiles were removed under reduced pressure to yield a brown solid, which was triturated with pentane to yield 4-(5-(2-amino-5-bromopyridin-3-yl)-1H-tetrazol-1-yl)-2,3-difluorophenol (Compound 1016) as a pale brown solid.

1. additionAfter the addition
2. temperaturethe reaction mixture was warmed to room temperature
3. customThe reaction was carefully quenched with crushed ice
4. extractionextracted with EtOAc (3×200 mL)
5. washThe combined organics were washed with water
6. washwashed with brine
7. dry with materialdried over sodium sulfate
8. filtrationAfter filtration
9. customthe volatiles were removed under reduced pressure
10. customto yield a brown solid, which
11. customwas triturated with pentane