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CAS No. : | 113118-84-6 | MDL No. : | MFCD03086178 |
Formula : | C12H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ACFVOZGSDCHVGJ-UHFFFAOYSA-N |
M.W : | 183.21 | Pubchem ID : | 15519764 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
EXAMPLE 11 5-Phenyl-3-pyridinecarboxaldehyde 5-Phenyl-3-(N-methoxy-N-methyl)pyridinecarboxamide (1.32 g, 5.45 mmol) was dissolved in THF (30 mL) under inert atmosphere, then cooled to -70 C. with stirring. Diisobutylaluminum hydride (11 mL of a 1M solution in cyclohexane, 11 mmol) was added. After addition was complete, the mixture was stirred at -70 C. for 2h. Saturated ammonium chloride solution (1 mL) was added to the reaction mixture, followed by water (15 mL) and chloroform (50 mL). The mixture was filtered through celite, the organic phase separated and the aqueous phase again extracted with chloroform (80 mL). The combined organic extracts were washed with water (2*50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo. The crude material was chromatographed on silica gel with ethyl acetate-hexane (2:3) as eluant to afford the title compound as an oil, 790 mg, 80%. LRMS (EI) m/e 185 (M+ +2), 184 (M+ +H), 183 (M+), 182 (M+ -H); 1 H NMR (CDCl3, 300 MHz): delta10.20 (s, 1H), 9.08 (d, J=2 Hz, 1H), 9.05 (d, J=2 Hz, 1H), 8.35 (t, J=2 Hz, 1H), 7.63 (m, 2H), 7.45-7.55 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium cyanoborohydride; In methanol; water; acetic acid; acetonitrile; | EXAMPLE 12 5-Phenyl-3-(N-pyrrolidinomethyl)pyridine <strong>[113118-84-6]5-Phenyl-3-pyridinecarboxaldehyde</strong> (400 mg, 2.18 mmol) and pyrrolidine (300 mg, 4.39 mmol) were dissolved in acetonitrile (20 mL) with stirring. The reaction mixture was chilled (0 C.), sodium cyanoborohydride (30 mg, 4.4 mmol) was added and the mixture stirred at 0 C. for 30 minutes. Glacial acetic acid (0.25 mL) was added dropwise and the mixture stirred at 25 C. for 18 h. 1M HCl (10 mL) and methanol (10 mL) were added and the mixture concentrated in vacuo. Water (20 mL) was added and the solution basified with solid sodium hydroxide. This was extracted with methylene chloride (3*30 mL) and the combined organic extracts were washed with water (20 mL), brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude material was chromatographed on silica gel with ethyl acetate-hexane (2:3) as eluant to afford the title compound as an oil, 360 mg, 70%. This was converted to the fumarate derivative of the title compound by the addition of one equivalent of fumaric acid to a methanol (10 mL) solution of the free amine at 25 C. After 30 minutes, the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether, followed by recrystallization from ethyl acetate afforded 5-phenyl-3-(N-pyrrolidinomethyl)pyridine fumarate; M.p. 126-127 C. (EtOAc); 1 H NMR (DMSO-d6, 300 MHz): delta8.82 (s, 1H), 8.62 (s, 1H), 8.20 (s, 1H), 7.72 (bs, 2H), 7.50 (bs, 3H), 6.58 (s, 2H), 4.15 (s, 2H), 2.97 (s, 4H), 1.85 (s, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 2.5h;Heating / reflux; | IA. S-Phenyl-pyridine-3-carbaldehyde: A biphasic mixture of 5- bromo-3-formyl pyridine (0.500 g, 2.69 mmol), Pd(Ph3P)4 (0.155 g, 0.134 mmol), and phenyl boronic acid (0.492 g, 4.03 mmol) in degassed 2.0 M aqueous Na2CO3 (6.0 mL) and toluene (6.7 mL) was heated at reflux for 2.5 h. The reaction was cooled to rt, diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (Ix). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give an orange- brown oil weighing 0.848 g. Column chromatography on silica gel gave 0.447 g (91%) of the biaryl compound as a pale yellow solid. 1H NMR (500 MHz, CDCl3) delta: 10.19 (s, IH), 9.07 (s, IH), 9.04 (s, IH), 8.34 (s, IH), 7.62 (d, J = 7.7 Hz, 2H), 7.52 (t, J = 7.7 Hz, 2H), 7.47-7.44 (m, IH). MS 184.2 (M+H)+; 216.2 (M+CH3OH+H)+. |