Reaktion #10505

Reaktionsgleichung

1-butyn-3-yl-2-methyl-pyrrolidine

CH3CN

1-But-3-ynyl-2-(R)-methyl-pyrrolidine

4-bromo-2-iodo-phenylamine

diisopropylamine

4-bromo-2-iodo-phenylamine

→

title compound

Ausbeute 97.3%

4-Bromo-2-[4-(2-(R)-methyl-pyrrolidin-1-yl)-but-1-ynyl]-phenylamine

Ausbeute 97.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas consumed
2. 2
   SonstigeThe solvent CH3CN was removed under vacuo
3. 3
   Extraktionthe residue was extracted with IPAC (500 mL) and 5% NaHCO3 (2×300 mL)
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of 1-butyn-3-yl-2-methyl-pyrrolidine in CH3CN (prepared in Example 65A assuming 100% conversion, 89 mmol) was added 4-bromo-2-iodo-phenylamine (12.0 g, 40 mmol) under nitrogen followed by addition of CuI (0.38 g, 2.0 mmol), PdCl2(PPh3) 2 (0.70 mg, 1.0 mmol) and diisopropylamine (33.6 mL, 240 mmol). The resulting solution was stirred at room temperature for 2 hours, at which time analytical HPLC analysis indicated that all 4-bromo-2-iodo-phenylamine was consumed. The solvent CH3CN was removed under vacuo and the residue was extracted with IPAC (500 mL) and 5% NaHCO3 (2×300 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give the title compound as a thick oil (11.96 g), which was used in the next step without further purification.

Quelle