Reaktion #1166411

Reaktionsgleichung

6-bromobenzothiazole

sodium carbonate

THF

→

title compound

Ausbeute 47.0%

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

Ausbeute 47.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefitted with a reflux condenser
2. 2
   Temperaturthe stirred mixture was heated at 80°, under nitrogen, for 24 h
3. 3
   TemperaturThe mixture was cooled
4. 4
   Waschenwashed with brine (2×25 mL)
5. 5
   TrocknenThe combined organic extracts were dried over sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified by silica gel chromatography (20% ethyl acetate/hexanes eluent)

Vorschrift

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid(178 mg, 0.65 mmol), tetrakis (triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 6-bromobenzothiazole (139 mg, 0.65 mmol), 0.65 mL of 2M aqueous sodium carbonate and 2 mL of THF, 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 (20% ethyl acetate/hexanes eluent) to give 106 mg (47%) of the title compound as an amorphous solid. mp 183°-187°. FDMS: m/e=362. α[D]589 =+87.80 (c=0.55, chloroform).

Quelle