반응 #452988

반응 방정식

sodium bicarbonate

5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine

1-hexyne

Water

→

oil

수율 64.0%

5-Hexynyl-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine

수율 64.0%

용매

NEt3

반응 조건

후처리

1. 1
   온도The mixture was refluxed overnight
2. 2
   추출The mixture was extracted with EtOAc, which
3. 3
   건조was dried over MgSO4
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The residue was chromatographed on a silica gel column
7. 7
   세척eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

실험 절차

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (272 mg, 1.00 mmol), bis(triphenylphosphine)palladium(II) chloride (18 mg, 0.025 mmol) and copper (I) iodide (2 mg, 0.025 mmol) in NEt3 (6.0 mL) was added 1-hexyne (0.237 mL, 2.00 mmol). The mixture was refluxed overnight and cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford an oil (174 mg, 64%). MS (CI/NH3) m/z 273 (M+H(+. 1H NMR (CDCl3, 300 MHz) δ 0.96 (t, J=7.0 Hz, 3H), 1.42-2.10 (m, 8H), 2.26-2.37 (m, 1H), 2.43 (t, J=7.0 Hz, 2H), 2.48 (s, 3H), 2.63-2.71 (m, 1H), 3.08-3.16 (m, 1H), 3.88-4.03 (m, 2H), 4.47-4.55 (m, 1H), 7.17-7.21 (m, 1H), 8.19-8.23 (m, 2H).

출처