HCID 59333306, compound → HCID 59333284, compound

Temperature

160 °C

To a stirred solution of 3-(1-Bromo-7-trifluoromethoxy-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol (1.00 g; 2.47 mmol; 1 eq) prepared as in example 51 step 2 in degassed N-methylpyrrolidone (10 mL) are successively added under argon tetrakis-triphenylphosphine palladium (570 mg; 0.49 mmol; 0.2 eq) and copper cyanide (885 mg; 9.90 mmol; 4 eq). The resulting solution is then heated at 160° C. for 3 hours until reaction is complete on TLC. The mixture is then quenched with an aqueous solution saturated with sodium hydrogenocarbonate (50 mL) and the resulting basic solution (pH>8) is extracted with ethyl acetate (100 mL). The organic layer is separated, washed with an aqueous solution saturated with sodium hydrogenocarbonate (50 mL), dried over sodium sulfate, filtered and concentrated under vacuum to afford a brown oil. Chromatography of this crude oil on silica gel (gradient of ethyl acetate/cyclohexane from 1:9 to 5:5) afforded the title compound contaminated by 21% of residual triphenylphosphine oxide. Therefore, the mixture was further purified by a second column chromatography (chloroform/ethyl acetate 7:3) yielding the pure title compound (424 mg; 1.21 mmol; 49%).

1. additionare successively added under argon tetrakis-triphenylphosphine palladium (570 mg; 0.49 mmol; 0.2 eq)
2. customThe mixture is then quenched with an aqueous solution saturated with sodium hydrogenocarbonate (50 mL)
3. extractionthe resulting basic solution (pH>8) is extracted with ethyl acetate (100 mL)
4. customThe organic layer is separated
5. washwashed with an aqueous solution saturated with sodium hydrogenocarbonate (50 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customto afford a brown oil

ORD record

ord-84699d298f7445ac9274897fe1b4cf70

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513250B2