반응 #1867510

반응 방정식

sodium bicarbonate

5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine

5,5-dimethyl-1,3-hexadiene

tri-o-tolylphosphine

→

title compound

수율 42.0%

5-(5,5-Dimethyl-1,3-hexadienyl)-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridin

수율 42.0%

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 ethyl acetate:hexane 1:3

실험 절차

To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine (600 mg, 1.59 mmol) in acetonitrile (5.0 mL) and triethylamine (4.5 mL) was added 5,5-dimethyl-1,3-hexadiene (228 mg), palladium acetate (39 mg) and tri-o-tolylphosphine (205 mg). 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 ethyl acetate:hexane 1:3 to afford the title compound (126 mg, 42% yield). MS (CI/NH3) m/z 307 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 1.42 (s, 9H), 1.55 (s, 9H), 2.24-2.42 (m, 2H), 3.88 (t, J=7.5, 2H), 4.13 (dd, J=3, 7.5, 1H), 4.29-4.41 (m, 1H), 5.97 (d, J=15, 1H), 6.22 (dd, J=9, 15, 1H), 6.67-6.78 (m, 2H), 7.45 (br s, 1H), 8.95 (d, J=3.0, 1H).

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