반응 #1244901

반응 방정식

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

수율 97.3%

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

수율 97.3%

반응 조건

후처리

1. 1
   기타was consumed
2. 2
   기타The solvent CH3CN was removed under vacuo
3. 3
   추출the residue was extracted with IPAC (500 mL) and 5% NaHCO3 (2×300 mL)
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated under reduced pressure

실험 절차

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.

출처