Water → HCID 86650236, compound

Temperature

-78 °C

1-bromo-6-(4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)imidazo[1,5-a]pyridine (50.0 mg, 0.118 mmol) was dissolved in ether (2 mL) in a 50 mL round bottomed flask under a nitrogen atmosphere. The solution was cooled down to −78° C. and treated with t-BuLi (1.7 M pentane solution, 0.15 mL, 0.255 mmol, 2.2 equiv.) for 5 min. To the mixture was added a solution of MeI (65.8 mg, 0.464 mmol, 4.0 equiv.) in ether (1 mL). The reaction was allowed to warm up to room temperature for 30 min. To the mixture was added H2O (30 mL) and the whole was extracted with EtOAc (30 mL×3). Combined organic layers were washed with brine (30 mL) and dried with Na2SO4. The solvent was removed under a reduced pressure to give a crude mixture. The crude mixture was purified by a preparative TLC (SiO2=1 plate, ether/hexane=1:3 Rf=0.4) to give 1-methyl-6-(4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)imidazo[1,5-a]pyridine as light yellow crystals.

1. temperatureto warm up to room temperature for 30 min
2. extractionthe whole was extracted with EtOAc (30 mL×3)
3. washCombined organic layers were washed with brine (30 mL)
4. dry with materialdried with Na2SO4
5. customThe solvent was removed under a reduced pressure
6. customto give a crude mixture
7. customThe crude mixture was purified by a preparative TLC (SiO2=1 plate, ether/hexane=1:3 Rf=0.4)

ORD record

ord-25a1c61550284200bb1c0d634522fa70

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952034B2