Morpholine → 4-(6-Chloro-4-iodopyridin-2-yl)morpholine
Reaction equation
C(N(CC)CC)C.Cl[C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[C:11]([Cl:16])[N:10]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[Cl:16][C:11]1[N:10]=[C:9]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:14]=[C:13]([I:15])[CH:12]=1Participants
4
Conditions
- Temperature
- 100 °C
Procedure
To a solution of triethylamine (1.0 equiv.) and 2,6-dichloro-4-iodopyridine (1.0 equiv.) at RT was added morpholine (1.0 equiv) in one portion, the resulting mixture was then heated in an oil bath at 100° C. for 18 hours. LCMS analysis indicated the formation of the desired product (M+H=324.9/326.8, Rt=0.98 min). Water was then added, and the mixture was extracted with ethyl acetate, and the combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was chromatographed via ISCO to yield 4-(6-chloro-4-iodopyridin-2-yl)morpholine as a light brown solid (63%). LCMS (m/z) (M+H)=324.9/326.8, Rt=0.98 min.