3-Iodo-2-methoxypyridine

Light yellow Cryst

General procedure: To a stirred, cooled (0 C) solution of 2, 2, 6, 6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) weresuccessively added BuLi (about 1.6 M hexanes solution, 1.5 mmol)and, 5 min later, ZnCl2TMEDA[51] (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (0.5 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (4 mL) and extraction with AcOEt (320 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatography on silica gel (the eluent is given in the product description) led to the compounds described below.General procedure: [Li(TMP)Zn(tBu)General procedure: To a stirred cooled (0 °C) solution of 2, 2, 6, 6-tetramethylpiperidine (1.0 mL, 6.0 mmol) in THF (5 mL) were added BuLi (1.6 M hexanes solution, 6.0 mmol) and, 5 min later, FeBrTo a solution of sodium methoxide (8.0 mL, 35.9 mmol, 4.0 eq, 25percent in methanol) in methanol (60 mL) was added 2-fluoro-3-iodo-pyridine (2.0 g, 8.97 MMOL). The reaction mixture was REFLUXED under argon for 1 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was removed at reduced pressure to give 1.8 G (85.4percent) of crude product as a YELLOW OIL. H-NMR (ACETONE-D6) S 8.16 (m, 2H), 6.78 (m, 1H), 3.93 (s, 3H); LC-MS (ES MH+ = 236.2) ; Rf = 0.75 (30percent ethyl acetate-hexane).Method H-8; Preparation of 3-iodo-2-methoxy-pvridine; To a solution of sodium methoxide (8.0 mL, 35.9 mmol, 4.0 eq, 25percent in methanol) in methanol (60 mL) was added 2-fluoro-3-iodo-pyridine (2.0 g, 8.97 mmol). The reaction mixture was refluxed under argon for 1 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was removed at reduced pressure to give 1.8 g (85.4percent) of crude product as a yellow oil.'H-NMR (Acetone-d6) 8 8.16 (m, 2H), 6. 78 (m, 1H), 3.93 (s, 3H); LC-MS (ES MH+ = 236.2) ; Rf = 0.75 (30percent ethyl acetate-hexane).Preparation of 3-iodo-2-methoxv-pvridine. To a solution of sodium methoxide (8.0 mL, 35.9 mmol, 4.0 eq, 25percent in methanol) in methanol (60 mL) was added 2-fluoro-3-iodo-pyridine (2.0 g, 8.97 mmol). The reaction mixture was refluxed under argon for 1 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was removed at reduced pressure to give 1.8 g (85.4percent) of crude product as a yellow oil.

Molecular Weight:235.02
XLogP3:1.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:234.94941
Monoisotopic Mass:234.94941
Topological Polar Surface Area:22.1
Heavy Atom Count:9
Complexity:89.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes