Hydrogen Peroxide → HCID 57657248, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL round bottom flask was charged with 1-isobutyl-8-vinyl-1H-imidazo[4,5-c]quinolin-4-amine (850 mg, 3.2 mmol) and 200 mL of tetrahydrofuran. The flask was purged with nitrogen. A solution of 9-borabicyclo[3.3.1]nonane (0.5M in tetrahydrofuran, 8.5 mL, 4.25 mmol) was added in one portion and the reaction was stirred overnight. Additional 9-borabicyclo[3.3.1]nonane (0.5M in tetrahydrofuran, 12.5 mL, 6.25 mmol) was added and the mixture was stirred for approximately 24 hours. The reaction was cooled to 0° C. with an ice/water bath and 30% H2O2 (2 mL) was added dropwise. After 5 minutes, 10% NaOH (5 mL) was added dropwise. The reaction was stirred for 30 minutes, diluted with water (100 mL) and then extracted with chloroform (3×100 mL). The combined organic fractions were concentrated under reduced pressure and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a gradient of 0-30% CMA in chloroform) followed by recrystallization from acetonitrile to provide 580 mg of 2-(4-amino-1-isobutyl-1H-imidazo[4,5-c]quinolin-8-yl)ethanol as an off-white solid, mp 214-216° C.

Provenance & Evidence