Reaction #1166333

Reaction equation

(+)-(4aR)-(10bR)-4-methyl-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

9-phenanthreneboronic acid

triethylamine

dimethyl ether

→

title compound

Yield 30.3%

(+)-(4aR)-(10bR)-4-methyl-8-(9-phenanthrenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Yield 30.3%

Solvents

chloroform

Conditions

Workup

1. 1
   Otherfitted with a reflux condenser
2. 2
   Temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24 h
3. 3
   TemperatureThe mixture was cooled
4. 4
   Washwashed with brine (2×25 mL)
5. 5
   DryingThe combined organic extracts were dried over sodium sulfate
6. 6
   Concentrationconcentrated
7. 7
   Otherpurified by silica gel chromatography (ethyl acetate eluent)

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (200 mg, 0.65 mmol), tetrakis (triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 9-phenanthreneboronic acid (173 mg, 0.78 mmol), triethylamine (0.2 mL, 1.3 mmol), and 2 mL of dimethyl ether, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. The mixture was cooled, diluted with chloroform (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent), to give 80 mg (30%) of the title compound as a white solid. mp 218°-220°. FDMS: m/e=405. α[D]589 =+63.01 (c=0.98, chloroform).

Source