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CAS No. : | 1222090-62-1 | MDL No. : | MFCD29054520 |
Formula : | C14H12BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 322.15 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With silver carbonate; In acetonitrile; at 65℃; for 18.0h; | Preparation 84: Methyl 2-(benzyloxy)-5-bromoisonicotinate To a suspension of methyl 5-bromo-2-oxo-1 ,2-dihydropyridine-4-carboxylate (2.5 g, 10.77 mmol) in MeCN (35 ml_) was added silver carbonate (4.46 g, 16.1 6 mmol) and benzyl bromide (1 .54 ml_, 12.93 mmol). The reaction mixture was heated to 65 C and stirred for 18 hours. The reaction mixture was filtered through a plug of Celite and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 50-100% DCM in cyclohexane to give the title compound (3.31 g, 95%). 1 H NMR (500 MHz, CDCI3): delta 8.38 (s, 1 H), 7.45 (dd, J = 8.0, 2.0 Hz, 2H), 7.41 -7.38 (m, 2H), 7.34 (m, 1 H), 7.17 (m, 1 H), 5.39 (s, 2H), 3.96 (s, 3H). LCMS (ESI) Rt = 3.04 minutes MS m/z 321 .97 [M+H]+ |
91% | With silver carbonate; at 50℃; | Intermediates H6A and H6BH6.1[0244] Methyl 2-(benzyloxy)-5-bromoisonicotinate (H6.1) To 2 mL of methyl5-bromo-2-oxo-1,2-dihydropyridine-4-carboxylate (232 mg, 1.00 mmol)(commercially available from Combi-Blocks) was added benzyl bromide (205 mg, 1.20 mmol) and silver carbonate (413 mg, 1.50 mmol) (commercially available from Sigma-Aldrich, St. Louis, MO, USA). The resulting mixture was stirred at 50C overnight. After reaction completion, the mixture was loaded onto a solid silica gel cartridge and purified by chromatography with 10% EtOAc/hexane to afford the desired product H6.1 (293 mg, 91%). MS ESI (pos.) m/e: 322.1 (M+H)+.H6.1 H6.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 70℃; for 18h;Inert atmosphere; | Preparation 85: (E)-methyl 2-(benzyloxy)-5-(2-ethoxyvinyl)isonicotinate To a suspension of methyl 2-(benzyloxy)-5-bromoisonicotinate (Preparation 84, 1 .5 g, 4.66 mmol), (E)-2-(2-ethoxyvinyl)-4, 4, 5, 5-tetramethyl-1 ,3,2-dioxaborolane (Preparation 29, 1 .844 g, 9.31 mmol) and Na2C03 (0.99 g, 9.31 mmol) in toluene (5 ml_), EtOH (5 ml_) and water (5 ml_) was added Pd(PPh3)4 (377 mg, 0.326 mmol). The reaction mixture was heated to 70C for 1 8 hours, under nitrogen. The reaction mixture was diluted with EtOAc (75 ml_) and water (75 ml_). The organic layer was dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-1 0% EtOAc in cyclohexane to give the title compound (1 .2 g, 82%). 1 H NMR (500 MHz, CDCI3): delta 8.23 (s, 1 H), 7.47 (d, J = 7.5, 1 .5 Hz, 2H), 7.39 (td, J = 8.5, 2.5 Hz, 2H), 7.33 (m, 1 H), 7.24 (s, 1 H), 6.80 (d, J = 13.0 Hz, 1 H), 6.39 (d, J = 13.0 Hz, 1 H), 5.40 (s, 2H), 3.95 (q, J = 7.5 Hz, 2H), 3.92 (s, 3H), 1 .37 (t, J = 7.5 Hz, 3H). LCMS (ESI) Rt = 3.09 minutes MS m/z 314.27 [M+H]+ |