반응 #1867491

반응 방정식

sodium bicarbonate

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

5,5-dimethyl-1,3-hexadiene

tri-o-tolylphosphine

→

oil

수율 75.0%

5-(5,5-Dimethyl-1,3-hexadienyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine

수율 75.0%

용매

acetonitrile

triethylamine

반응 조건

후처리

1. 1
   온도the resulting mixture was cooled to room temperature
2. 2
   추출the mixture was extracted with EtOAc
3. 3
   건조dried (MgSO4)
4. 4
   농축concentrated
5. 5
   기타The residue was chromatographed on a silica gel column
6. 6
   세척eluting with CHCl3 /MeOH 10:1

실험 절차

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (272 mg, 3.0 mmol) in acetonitrile (3.0 mL) and triethylamine (2.5 mL) was added 5,5-dimethyl-1,3-hexadiene (0.50 mL), palladium acetate (23.0 mg, 0.1 mmol) and tri-o-tolylphosphine (122 mg, 0.1 mmol). After being heated in a sealed tube at 100° C. overnight, the resulting mixture was cooled to room temperature. Minimum amount of saturated sodium bicarbonate was added to free the amine hydrochloride salt, and the mixture was extracted with EtOAc, dried (MgSO4), and concentrated. The residue was chromatographed on a silica gel column, eluting with CHCl3 /MeOH 10:1 to afford a light yellowish oil (225 mg, 75%). MS (CI/NH3) m/z 301 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.08 (S, 9H), 1.55-1.77 (m, 3H), 1.98-2.10 (m, 1H), 2.37-2.47 (m, 1H), 2.50 (s, 3H), 2.64-2.73 (m, 1H), 3.07-3.17 (m, 1H), 3.90-4.06 (m, 2H), 5.93 (d, J=15.5 Hz, 1H), 6.16 (dd, J=15.5, 9.9 Hz, 1H), 6.42 (d, J=15.5 Hz, 1H), 6.78 (dd, J=9.9, 15.5 Hz, 1H), 7.21 (dd, J=3.0, 1.5 Hz, 1H), 8.14 (d, J=3.0 Hz, 1H), 8.19 (d, J=1.5 Hz, 1H).

출처