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CAS No. : | 1121-55-7 | MDL No. : | MFCD02178019 |
Formula : | C7H7N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DPZYLEIWHTWHCU-UHFFFAOYSA-N |
M.W : | 105.14 | Pubchem ID : | 14272 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 34.33 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.87 cm/s |
Log Po/w (iLOGP) : | 1.61 |
Log Po/w (XLOGP3) : | 1.51 |
Log Po/w (WLOGP) : | 1.62 |
Log Po/w (MLOGP) : | 1.05 |
Log Po/w (SILICOS-IT) : | 2.17 |
Consensus Log Po/w : | 1.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.93 |
Solubility : | 1.23 mg/ml ; 0.0117 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.39 |
Solubility : | 4.29 mg/ml ; 0.0408 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.4 |
Solubility : | 0.419 mg/ml ; 0.00398 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
Signal Word: | Danger | Class: | 6.1,3,8 |
Precautionary Statements: | P210-P233-P240-P241+P242+P243-P260-P262-P264-P270-P271-P272-P273-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P370+P378-P391-P403+P233-P405-P501 | UN#: | 3073 |
Hazard Statements: | H225-H301-H310-H314-H317-H335-H411 | Packing Group: | Ⅱ |
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 |
---|---|---|
80% | With sodium amide In diethyl ether at 0 - 20℃; | |
78% | Stage #1: Methyltriphenylphosphonium bromide With lithium diisopropyl amide In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere; Stage #2: 3-pyridinecarboxaldehyde In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; | 3-Vinylpyridine (2) To a solution of diisopropylamine (2.64 ml, 18.7 mmol) in THF (94 ml) at -78 °C was added BuLi (1.6 M, 11.7 ml) and the mixture was warmed to 0 °C for 10 min before cooling back to - 20°C. Triphenylmethylphosphonium bromide (6.68 g, 18.7 mmol) was then added and the mixture was stirred for 30 min. The ylide thus obtained was cooled to -78 °C and nicotinaldehyde (1.76 ml, 18.7 mmol) was then added dropwise and the resulting mixture was allowed to warm to room temperature for 1 h. The reaction was quenched with water (50 ml) and extracted with Et2O (2 x 50 ml). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica (1:1 MTBE:hexanes) gave 2 (1.46 g, 78%) as a light-sensitive oil. Spectroscopic data was consistent with literature data:[2] 1HNMR (CDCl3, 500 MHz): δ 8.62 (d, J = 2.5 Hz, 1H), 7.74 (dt, J = 2, 7.5 Hz, 1H), 7.26 (m, 1H), 6.71 (dd, J = 11, 7 Hz, 1H), 5.83 (dd, J = 0.5, 17 Hz, 2H), 5.39 (d, J = 11 Hz, 1H). 13C NMR (CDCl3, 125 Hz): 148.7, 148.1, 134.0 133.3, 132.6, 123.3, 116.2. |
77% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -20℃; for 0.5h; Stage #2: 3-pyridinecarboxaldehyde In tetrahydrofuran; hexane at -60 - 20℃; Further stages.; |
65% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium; diisopropylamine In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Stage #2: 3-pyridinecarboxaldehyde In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; | |
44% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 4h; Inert atmosphere; Stage #2: 3-pyridinecarboxaldehyde In tetrahydrofuran; hexane at 20℃; | |
With potassium <i>tert</i>-butylate In tetrahydrofuran Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With 1,2,2,6,6-pentamethylpiperidine; palladium diacetate; tris-(o-tolyl)phosphine In acetonitrile at 95℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 1.33333h; Microwave irradiation; | |
81% | With 2C8H8NO2(1-)*2Cl(1-)*2Pd(2+); tetrabutylammomium bromide; potassium carbonate In water at 120℃; for 0.5h; Sealed vessel; Microwave irradiation; | |
72% | With caesium carbonate; triphenylphosphine In tetrahydrofuran; water at 85℃; for 22h; |
66% | With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In water; isopropyl alcohol for 2h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.3349 g | In water at 140℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With C18H21N3O2Pd; tetrabutylammomium bromide; caesium carbonate In N,N-dimethyl acetamide at 150℃; for 15h; Sealed tube; | 4.1 Typical procedure for Heck reaction of vinyl heterocycles with aryl bromides General procedure: The 15 mL sealed tube was charged with aryl bromides (0.8 mmol), alkenes (0.5 mmol), Cs2CO3 or LiOtBu (0.7 mmol), TBAB (0.5 mmol) and the catalyst (1.2 mol%, 5.0 mg), in N,N-dimethylacetamide (2.0 mL). The reaction mixture was heated at 150 °C for 15 h and the progress of reaction was monitored by TLC. At the end of the reaction, the reaction mixture was cooled to room temperature and was diluted with EtOAc (20 mL), washed with 1N aq HCl and water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the Heck product in high purity. |
0.2667 g | In water at 140℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium hydroxide In water at 140℃; for 3h; | |
96% | Stage #1: Triethoxyvinylsilane With sodium hydroxide In water at 20℃; for 0.0833333h; Sealed tube; Stage #2: 3-Bromopyridine With palladium diacetate In water at 140℃; for 3h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.3467 g | In water at 140℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With tetraethylammonium chloride In DMF (N,N-dimethyl-formamide) at 70℃; for 72h; | A.6.1 To a solution of 3-BROMOPYRIDINE (2.49 g, 15.77 mmol) in DMF (50 mL) was added VINYLTRIBUTYLTIN (5.00 g, 15.77 mmol), tetraethylammonium chloride (2.61 g, 15.77 MMOL), and dichlorobistriphenylphosphine palladium (0.332 G, 0.473 mmol), and the solution was heated to 70° C for 3 days. The reaction was then diluted with water, and extracted into EtOAc 3 times. The organic extract was then dried and concentrated, and the crude product purified by chromatography (gradient 9: 1 hexanes: EtOAc to 4: 6 hexanes: EtOAc) to yield 1.026 g (62%) of the title COMPOUND. HNMR (400 MHZ, CDCI3) : 8 5.35 (dd, 1H, J=2.2, 11.0 Hz), 5.79 (d, 1H, J=17. 6 Hz), 6.66 (dd, 1H, J=11. 0,17. 8 Hz), 7.23 (m, 1H), 7.70 (d, 1H, J=7.6 Hz), 8.45 (d, 1H, J=4.9 Hz), 8.59 (s, 1H). |
30% | In N,N-dimethyl-formamide at 20 - 80℃; Inert atmosphere; | 8 Example 8 Preparation of 3 -vinyl pyridine[0373] The title compound was prepared by following general procedure 2 3-Bromo pyridine (3 0 g, 18 9 mmol) was dissolved in DMF (9 mL), tϖbutylvinyltin (6 62 g, 20 8 mmol) and Pd(PPli3)4 (0 326 g, 0 282 mol) was added to this solution at RT under nitrogen and heated at 80 0C for 3 h The reaction mixture was cooled to RT, diluted with water (90 mL) and extracted with DCM (3 x 150 mL) The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure below 400C The crude was purified through column chromatography (5% ethylacetate hexane in silica 100-200 mesh, Diameter of column - 5 0 cm, Height of silica - approx 5 inch) to provide the desired compound as a light yellow liquid (0 62 g, 30% yield) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: 3-vinylpyridine With AD-mix-α; water In <i>tert</i>-butyl alcohol at 0 - 20℃; for 48h; Stage #2: With sodium sulfite In <i>tert</i>-butyl alcohol at 0 - 20℃; for 1h; | A.6.2 A solution of ADmix alpha (4.83 g, 6.20 mmol) in t-BuOH: H20 1: 1 (50 mL) was poured into 3-vinylpyridine (0.36 g, 3.42 mmol) at 0 °C, and the solution was allowed to warm to room temperature. The reaction was covered with aluminum foil to exclude light and then stirred at room temperature for two days. The mixture was then cooled to 0 °C and sodium sulfite (5.503 g) was added. The mixture was then stirred at room temperature for 1 hour. EtOAc (100 ML) was added, and the layers were separated. The aqueous layer was then extracted with EtOAc twice more and CH2CI2 : MeOH 10: 1 once. The combined organic layers were then dried, and concentrated. The product (0.330 g, 69%) was pure by IC/MS (EI) : m/z 140.3 (M + 1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hexamethyldisilazane In tetrahydrofuran | 210.D EXAMPLE 210E 3-Vinylpyridine EXAMPLE 210E 3-Vinylpyridine To a slurry of methyltriphenylphosphine chloride (18.0 g, 50.5 mmol) in THF (20 mL) was added slowly sodium bis(trimethylsilyl)amide (1.0 M solution in THF, 50 mL). After the mixture was stirred at room temperature for 30 minutes, the reaction was cooled to 0° C., and 3-pyridinecarboxaldehyde (4.72 mL, 50.0 mmol) was added slowly to the mixture. After 30 minutes, the reaction mixture was diluted with ether (100 mL) and filtered through silica gel (100 g), rinsed with ether, and concentrated in vacuo. The resulting liquid was diluted with 1:1 hexane-ether (50 mL), and was again filtered through silica gel (50 g), rinsed with 70:30 ether-hexane and concentrated in vacuo to give3-vinylpyridine (4.31 g, 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium acetate In N,N-dimethyl acetamide at 140℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium hydroxide In water at 120℃; for 0.25h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium acetate In N,N-dimethyl acetamide at 140℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 6h; | O [00295] A 50 mL round bottom flask charged with tert-butyl 4-(5-cyclopropyl-3-iodo-l-(4-methoxybenzyl)-lH-pyrazolo[3,4-b]pyridin-4-yl)piperazine-l-carboxylate (500 mg, 0.85 mmol), triethylamine (355 μL, 2.54 mmol), Pd2dba3 (19.4 mg, 0.021 mmol), tri-o- tolylphosphine (19.4 mg, 0.064 mmol), and DMF (7 mL) was purged under N2 (3 cycles). 3- vinylpyridine (270.24 mg, 1.7 mmol) was added, and the mixture was stirred at 1000C under a N2 atmosphere for 6 hours. The reaction mixture was cooled to room temperature, diluted with warm EtOAc (100 mL) and washed with water (2 X 30 mL). The phases were separated, and the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (Biotage Flash 40S+) eluting with 25% EtOAc/hexane followed by 50% EtOAc/hexane to provide (E)-tert-butyl 4-(5-cyclopropyl-l-(4- methoxybenzyl)-3 -(2-(pyridin-3 -yl)vinyl)- 1 H-pyrazolo [3 ,4-b]pyridin-4-yl)piperazine- 1 - carboxylate (390 mg, 81% yield) as a solid. LCMS (APCI+) m/z 567.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38.3% | Stage #1: 2-chloro-11-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 20℃; for 0.166667h; Stage #2: 3-vinylpyridine In 1-methyl-pyrrolidin-2-one at 80℃; for 12h; | 100 Powdered potassium hydroxide (0.4 g, 0.00715 mol) was added to a solution of 2- Chloro-l l-methyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole (0.22 g. 0.000894 mol) in N-methyl 2-pyrolidone (1.0 mL) and stirred for 10 min at RT. 3-vinylpyridine (0.281 g, 0.00 268 mol) was added and stirred for further 12h at 8O°C. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 xlOO mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator. The crude product was purified through column chromatography (8% Methanol/dichloromethane in silica 100- 200 mesh, Diameter of column - 2.5cm, Height of silica - approx. 5inch), and further purified by preparative HPLC to yield the desired compound (free base) as yellow oil (0.120 g, 38.3% yield). The free base (0.060 g, 0.00017 mol) was dissolved in THF (1.0 mL). A solution of oxalic acid dihydrate (0.021 g, 0.00017 mol) in THF (1.0 mL) was added and stirred for 30 min at RT. The precipitate was filtered, washed with ether and dried to provide the oxalate salt of product as light yellow solid (0.035 g, 46.5% yield). The NMR data for the compound is as follows: 1H NMR (CD3OD) - 8.38 (s, 1H), 7.98-7.93 (d, 1H), 7.56-7.53 (m, 2H), 7.51-7.33 (m, 2H), 7.14-7.11 (dd, 1H), 5.01-4.98 (m, 1H), 4.65-4.13 (m, 3H), 3.45-3.35 (m, 1H), 3.2-3.1 (m, 2H), 2.91 and 2.65 (s, 3H), 2.6-2.5 (m, 1H), 2.5-2.49 (m, 1H), 2.4-2.3 (m, 1H), 2.25-2.1 (m, 1H), 1.65-1.5 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | Stage #1: 2-methyl-11-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 20℃; for 0.166667h; Stage #2: 3-vinylpyridine In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; | 99 Powdered potassium hydroxide (0.376 g, 0.0049 mol) was added to a solution of 2,11- dimethyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole (0.19 g. 0.00084 mol) in N- methyl 2-pyrolidone (1.3 mL) and allowed to stir for 10 min at RT. 3-vinyl pyridine (0.264 g, 0.00252 mol) was added and stirred for further 4 h at 80 °C. The reaction was monitored by TLC. Upon completion, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator. The crude was semi- purified through column chromatography (7% Methanol/dichloromethane in silica 100-200 mesh, Diameter o f column - 2.5cm, Height of silica - approx. 5inch), and further purified by preparative HPLC to yield the desired compound (free base) as yellow oil (0.080 g, 29% yield). The free base (0.040 g, 00012 mol) was dissolved in THF (1.0 mL). A solution of oxalic acid dihydrate (0.015 g, 0.00012 mol) in THF (1.0 mL) was added and stirred for 30 min at RT. The precipitate obtained was filtered, washed with ether and dried to obtain the product as oxalate salt (0.018 g, 36% yield). The NMR data for the compound is as follows: 1H NMR (CD3OD) - 8.4 (s, 1H), 7.9 (d, 1H), 7.5 (d, 1H), 7.3 (m, 3H), 7.1 and 7.05 (d, 1H), 5.0 (m, 1H), 4.5 (m, 2H), 4.3 (m, 1H), 3.7 (m, 1 H), 3.4 (m, 2 H), 3.2-3.1 (m, 1 H), 2.9 and 2.6 (s, 3 H), 2.5 and 2.4 (s, 3 H), 2.3 (m, 2 H), 2.2 (m, 1 H), 1.6 (m, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrabutylammonium sulfate; potassium hydroxide In water; dimethyl sulfoxide at 80℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrabutylammonium sulfate; potassium hydroxide In water; dimethyl sulfoxide at 80℃; Inert atmosphere; | ||
Stage #1: 2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 20℃; for 0.166667h; Stage #2: 3-vinylpyridine In 1-methyl-pyrrolidin-2-one at 100℃; for 18h; | 59 Example 59 Preparation of Compound No. 61 Example 59 Preparation of Compound No. 61 (1270) To a solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.1 g, 0.49 mmol) in N-methyl-2-pyrrolidone (0.5 mL) was added powdered potassium hydroxide (0.274 g, 4.9 mmol) and the reaction mixture was stirred for 10 min at RT. 3-Vinyl pyridine (0.26 g, 2.49 mmol) was added and stirring was continued for further 18 h at 100° C. After consumption of starting material (TLC), the reaction mixture was diluted with water (15 mL) and extracted with EtOAc (3×50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (eluent 7% MeOH: DCM) followed by preparative TLC, to obtain desired compound as yellow oil (0.040 g, 26% yield). (1271) 1H NMR (DMSO, Oxalate salt) δ (ppm): 8.4 (s, 1H), 8.3 (s, 1H), 7.55 (s, 2H), 7.35 (d, 1H), 7.25 (bs, 1H), 7.2 (s, 1H), 4.35 (bs, 4H), 3.5 (bs, 2H), 3.0 (m, 2H), 2.9 (m, 5H), 2.45 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With C18H16Cl2O4Pd2; caesium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In N,N-dimethyl-formamide at 120℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium tetrachloropalladate(II); cataCXium F sulf; potassium carbonate In water at 100℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium tetrachloropalladate(II); cataCXium F sulf; potassium carbonate In water at 100℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With palladium diacetate; (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane In ethanol; acetonitrile at 80℃; for 24h; Inert atmosphere; | 23 Under N2 protection, 3-ethynylpyridine (0.20 mmol) and Pd(OAc) 2 (0.02 mmol, were added to a 15 ml pressure-resistant tube.4.48 mg), R, R-DIPAMP (0.2 mmol, 18.32 mg), 95% EtOH (10 mmol, 595L) and CH3CN (1.5 mL).After completion of the reaction, the mixture was cooled to room temperature, and ethyl acetate (10 mL) was evaporated. The crude product was separated and purified by column chromatography to give 3-vinylpyridine, 15.8 mg of colorless liquid, yield 75%. |
Stage #1: 3-Ethynylpyridine With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diisobutylaluminium hydride In tetrahydrofuran at 0 - 22℃; Inert atmosphere; Stage #2: With water; rochelle salt In tetrahydrofuran at 0℃; for 0.5h; | ||
98 %Chromat. | With hydrogen In ethanol at 20℃; for 3.2h; Schlenk technique; Sealed tube; chemoselective reaction; |
83 %Chromat. | With hydrogen In acetonitrile at 110℃; for 15h; chemoselective reaction; | |
99.5 %Chromat. | With hydrogen In methanol; dimethyl sulfoxide at 25℃; for 2.5h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With triethylamine In N,N-dimethyl-formamide at 130℃; for 0.25h; Sealed vessel; Inert atmosphere; microwave irradiation; | 105.1 N-(3 -((4-(3 -bromophenoxy)benzyl)(4-cyanobenzy l)am ino)-2-methy lphenyl) methanesulfonamide (20 mg, 0.03 mmol), 3-vinylpyridine (7 mg, 0.07 mmol), palladium acetate (0.8 mg, 0.001 mmol), tri-ø-tolylphosphine (1.1 mg, 0.003 mmol), triethylamine (14 μL, 0.1 mmol) and DMF (0.5 mL) were mixed in a microwave vessel which was sealed and purged with N2. The vial was heated to 130 0C for 15 minutes.Water and CH2Cl2 were added, the mixture was filtered through a phase separator, the organic phase was evaporated and the residue was purified by preparative HPLC using 30-75 % AcCN/0.05 % aqueous HCOOH, (pH2.8), 25 mL/min, 25 minutes gradient. Yield 3 mg (14%).IH-NMR (acetone-d6, 500MHz): 8.76 (d, IH, J=1.6Hz), 8.46 (m, IH), 8.00 (m, IH), 7.68 (m, 2H), 7.54 (m, 2H), 7.42-7.26 (m, 8H), 7.17 (d, IH, J=7.6Hz), 7.11-7.04 (m, 2H), 6.96 (m, 2H), 6.91 (m, IH), 4.26 (s, 2H), 4.14 (s, 2H), 2.94 (s, 3H) and 2.53 (s,3H);MS (ESI) mlz 601.2 (M + H), 599.2 (M - H). |
14% | With triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 0.25h; Inert atmosphere; microwave irradiation; sealed vessel; | 105.1 N-(3-((4-(3-bromophenoxy)benzyl)(4-cyanobenzyl)amino)-2-methylphenyl)methanesulfonamide (20 mg, 0.03 mmol), 3-vinylpyridine (7 mg, 0.07 mmol), palladium acetate (0.8 mg, 0.001 mmol), tri-o-tolylphosphine (1.1 mg, 0.003 mmol), triethylamine (14 μL, 0.1 mmol) and DMF (0.5 mL) were mixed in a microwave vessel which was sealed and purged with N2. The vial was heated to 130° C. for 15 minutes. Water and CH2Cl2 were added, the mixture was filtered through a phase separator, the organic phase was evaporated and the residue was purified by preparative HPLC using 30-75% AcCN/0.05% aqueous HCOOH, (pH2.8), 25 mL/min, 25 minutes gradient. Yield 3 mg (14%).1H-NMR (acetone-d6, 500 MHz): 8.76 (d, 1H, J=1.6 Hz), 8.46 (m, 1H), 8.00 (m, 1H), 7.68 (m, 2H), 7.54 (m, 2H), 7.42-7.26 (m, 8H), 7.17 (d, 1H, J=7.6 Hz), 7.11-7.04 (m, 2H), 6.96 (m, 2H), 6.91 (m, 1H), 4.26 (s, 2H), 4.14 (s, 2H), 2.94 (s, 3H) and 2.53 (s, 3H);MS (ESI) m/z 601.2 (M+H), 599.2 (M-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-vinylpyridine; 7-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole With sodium t-butanolate In 1,4-dioxane at 85℃; for 18h; Inert atmosphere; Sealed tube; Stage #2: With magnesium sulfate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere; Sealed tube; | 34 Example 34; 7-[(E)-2-pyridin-3-ylvinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indoleA mixture of bis(tri-t-butylphosphino)palladium (18.4 mg, 0.036 mmol; Strem), 3-vinylpyridine (123 mg, 0.52 mmol; TCI-US), sodium t-butoxide (87 mg, 0.90 mmol; Aldrich) and the product of Example 1B (105 mg, 0.36 mmol) was combined with 1,4-dioxane (2 mL). The mixture was purged with a stream of nitrogen for 2 minutes, then stirred at 85° C. in a sealed tube. After 18 hours, the reaction mixture was cooled to ambient temperature. Magnesium sulfate (43 mg, 0.36 mmol) and 3-vinylpyridine (85 mg, 0.36 mmol; TCI-US) were added and the reaction mixture was again purged with nitrogen, sealed and stirred at 100° C. for 24 hour in a sealed tube. The reaction mixture was cooled to ambient temperature, filtered through a glass microfiber frit, rinsed with methanol (2 mL) and purified by reverse-phase HPLC [Waters XBridge RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 30-100% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 2.01-2.18 (m, 4H), 3.02-3.12 (m, 2H), 3.14 (pent, J=3.4 Hz, 1H), 3.20-3.29 (m, 2H), 4.23 (s, 2H), 7.03 (t, J=7.6 Hz, 1H), 7.25 (d, J=16.5 Hz, 1H), 7.27 (d, J=7.3 Hz, 1H), 7.41 (d, J=7.3 Hz, 1H), 7.43 (dd, J=8.2, 4.9 Hz, 1H), 7.74 (d, J=16.5 Hz, 1H), 8.07-8.15 (m, 1H), 8.38 (dd, J=4.6, 0.9 Hz, 1H), 8.75 (d, J=1.5 Hz, 1H); MS (APCI) m/z 316 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tetrabutyl ammonium fluoride; palladium dichloride In tetrahydrofuran at 65℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tetrabutylammonium sulfate; potassium hydroxide In water; dimethyl sulfoxide at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tetrabutylammonium sulfate; potassium hydroxide In water; dimethyl sulfoxide at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 60℃; for 3h; Inert atmosphere; | Acetate 10 To a solution of 2 (50 mg, 0.48 mmol) and 9 (0.76 ml, 4.76 mmol) in toluene (4 ml) was added Grubbs‘ catalyst 7 (40 mg, 0.04 mmol) and the mixture was warmed to 60 °C for 3 h. The reaction was cooled to room temperature and concentrated in vacuo. Purification by flash column chromatography on silica (4:1 to 1:1 EtOAc:hexanes) gave 10 (72 mg, 85%) as an oil. Spectroscopic data was consistent with literature data:[3] 1H NMR (CD3Cl, 500 MHz): δ 8.61 (d, J = 2.5 Hz, 1H), 8.49 (dd, J = 1.5, 3 Hz, 1H), 7.71 (dt, J = 2.5, 4 Hz, 1H), 7.26 (m, 1H), 6.64 (d, J = 16 Hz, 1H), 6.36 (dt, J = 6.0, 3.5 Hz, 1H), 4.75 (dd, J = 1.5, 4,5 Hz, 2H), 2.12 (s, 3H). 13C NMR (CD3Cl, 75 MHz): 170.7, 148.9, 148.3, 133.1, 130.1, 125.7, 77.5, 76.6, 64.6, 21.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: 3-vinylpyridine In dichloromethane for 24h; Darkness; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 4h; | |
Multi-step reaction with 2 steps 1: sodium azide; Iodine monochloride / acetonitrile; dichloromethane / 1 h / -20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / diethyl ether / 1.5 h / 0 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: iodine(I) azide / acetonitrile / 5 h / 0 °C 2: potassium <i>tert</i>-butylate / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrabutylammomium bromide; sodium hydroxide at 100℃; for 18h; | 2 Example 2: Preparation of Compound Nos. 2, 2a and 2b Example 2: Preparation of Compound Nos. 2, 2a and 2b [0151] To a solution of 2,3,5,6,7,1 lc-hexahydro-lH-indolizino[7,8-b]indole (400 mg, 1.88 mmol) in 60 % aq. NaOH (5 mL) was added 3-vinyl pyridine (396 mg, 3.77 mmol) and tetrabutyl ammonium bromide (607 mg, 1.88 mmol). The reaction mixture was allowed to stir at 100 °C for 18 h. The progress of reaction was monitored by TLC and LCMS. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2x100 mL). The combined organic layer was washed with water (4x50 mL) and dried over sodium sulfate. Removal of EtOAc under reduced pressure gave a crude product that was purified by reverse phase HPLC to afford 60 mg of 2,3,5,6,7,1 lc-hexahydro-7- (2- (pyridin-3-yl)ethyl)-lH- indolizino[7,8-b]indole. The stereoisomers were separated by chiral HPLC. 1H NMR (CDCI3, freebase) δ (ppm): 8.46 (s, 1H), 8.30 (s, 1H), 7.50 (d, 1H), 7.15-7.25 (m, 3H), 7.06- 7.18 (m, 2H), 4.21-4.36 (m, 1H), 3.18-3.30 (m, 1H), 2.98-3.10 (m, 2H), 2.71-2.95 (m, 2H), 2.38-2.58 (m, 2H), 2.15-2.28 (m, 1H), 1.80-1.95 (m, 2H), 1.20-1.27 (m, 3H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; | 6.1.1 Step 1 : To a solution of 4-(5-chloropyridin-3-yl)-7-iodo-5-((irans-4- methylcyclohexyl)methyl)-5H-pyrrolo[3,2-(^pyhmidine-2-carbonitrile (Preparative Example 5.3, 391 mg, 0.796 mmol), 3-vinylpyhdine (0.17 mL, 1 .59 mmol), and triethylamine (0.22 mL, 1 .59 mmol) in DMF (8.0 mL) were added Pd2(dba)3 (36.4 mg, 0.0398 mmol) and P(o-tol)3 (24.2 mg, 0.0796 mmol), and the mixture was heated at 100 °C for 1 hour under a nitrogen atmosphere. The reaction was then cooled to room temperature, diluted with water (30 mL), and extracted with ethyl acetate (3 χ 20 mL). The combined organic layers were washed with water (2 * 50 mL) and brine (30 mL), dried over anhydrous Na2S04, filtered, and concentrated. Purification of the residue on a silica gel column (0 to 100% EtOAc/dichloromethane) afforded 4-(5-chloropyridin-3-yl)-5-((irans-4- methylcyclohexyl)methyl)-7-((£)-2-(pyridin-3-yl)vinyl)-5/-/-pyrrolo[3,2-c/]pyrimidine-2- carbonitrile. MS APCI calc'd. for C27H25CIN6 [M + H]+ 469, found 469. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: 6,6,7,7-tetrabromo-4,5-dimethyl-1,3-dithiole-2-one With sodium iodide In acetonitrile at 70℃; for 5h; Inert atmosphere; Stage #2: 3-vinylpyridine In acetonitrile at 70℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With eosin In acetonitrile at 20℃; for 16h; Irradiation; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: 3-Bromopyridine With magnesium; lithium chloride In tetrahydrofuran at 0 - 20℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: vinyl acetate With iron(III) chloride In tetrahydrofuran at 0℃; for 3h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With diethoxymethylane; (4,4’-bi-1,3-benzodioxole)-5,5-diylbis(di(3,5-di-tertbutyl-4-methoxyphenyl)phosphine); copper diacetate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Glovebox; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58 mg | With tetrabutyl ammonium fluoride; sodium hydroxide at 100℃; for 18h; | 114 Example 114 Preparation of Compound Nos. 134 and 134a-b Example 114 Preparation of Compound Nos. 134 and 134a-b (1330) A mixture of 9-methyl-2,3,4,5,6,10c-hexahydro-1H-3a,6,7-triaza-cyclopenta[c]fluorene (100 mg, 0.44 mmol), 3-vinyl-pyridine (185 mg, 1.762 mmol), tetrabutylammonium bromide (425 mg, 1.32 mmol) and 50% NaOH solution (6 mL) was stirred at 100° C. for 18 h. The progress of reaction was monitored by TLC and LCMS. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to yield 9-methyl-6-(2-pyridin-3-yl-ethyl)-2,3,4,5,6,10c-hexahydro-1H-3a,6,7-triaza-cyclopenta[c]fluorene (58 mg). 1H NMR (CDCl3, freebase) δ (ppm): 8.41 (d, 1H), 8.27 (s, 1H), 8.07 (s, 1H), 7.58 (s, 1H), 7.2 (d, 1H), 7.1 (dd, 1H), 4.4 (m, 2H), 3.99 (bs, 1H), 3.2 (dd, 1H), 3.17 (t, 2H), 2.84-2.7 (m, 3H), 2.5 (m, 1H), 2.41 (s, 3H), 2.2 (dd, 1H), 1.9 (m, 4H). Separation by chiral HPLC provided enantiomers 134a and 134b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | Stage #1: 8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 20℃; for 0.166667h; Stage #2: 3-vinylpyridine In 1-methyl-pyrrolidin-2-one at 100℃; for 18h; | 58 Example 58 Preparation of Compound No. 60 Example 58 Preparation of Compound No. 60 (1269) To a solution of 8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.2 g, 0.9 mmol) in N-methyl-2-pyrolidone (1.5 mL) was added powdered potassium hydroxide (0.507 g, 9.0 mmol). The reaction mixture was stirred for 10 min at RT. 3-Vinyl pyridine (0.3 g, 2.8 mmol) was added and the reaction mixture was stirred at 100° C. for 18 h. After consumption of starting material (TLC), the reaction mixture was diluted with water (15 mL) and extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography over silica gel (eluent 8% MeOH: DCM) followed by preparative TLC to obtain the desired compound as a yellow oil (0.032 g, 11% yield). 1H NMR (DMSO, Oxalate salt) δ (ppm): 8.4 (d, 1H), 8.3 (s, 1H), 7.57 (d, 2H), 7.49 (d, 1H), 7.26 (m, 1H), 7.10 (d, 1H), 4.45 (m, 4H), 3.5 (bs, 2H), 3.0 (t, 2H), 2.95 (m, 2H), 2.90 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18 mg | With palladium diacetate; In N,N-dimethyl-formamide; | Example 0807 0807-1 A mixture of 3-bromo-1-methyl-1H-pyrazole (100 mg), 3-vinylpyridine (100 muL), triethylamine (173 muL), palladium acetate(II) (14 mg), tri(o-tolyl)phosphine (76 mg), and N,N-dimethylformamide (3.1 mL) was stirred at 140 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and purified by silica gel column chromatography (hexane-ethyl acetate-methanol, NH silica), thereby obtaining (E)-3-(2-(1-methyl-1H-pyrazol-3-yl)vinyl)pyridine (18 mg) as pale yellow oily substance. MS m/z (M+H): 186. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With platinum on carbon; potassium <i>tert</i>-butylate; hydrogen In toluene for 12h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Methyldicyclohexylamine; palladium diacetate; XPhos In 1,4-dioxane at 100℃; Sealed tube; | 1-9 4-[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-2-methyl-5-[(E)-2-(pyridin-3-yl)ethenyl]pyrimidine (TT1) A solution of MM3 (200 mg, 0.57 mmol), 3-vinylpyridine (90 mg, 0.86 mmol), X-Phos (27.2 mg, 0.057 mmol), and Pd(OAc)2 (6.41 mg, 0.028 mmol) in 1,4-dioxane (2.8 mL) was treated with N,N-dicyclohexylmethyl amine (223 mg, 1.14 mmol). The reaction vessel was sealed and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, diluted with EtOAc (30 mL), and washed with saturated aqueous NaHCO3 (35 mL) and brine (35 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (0% to 100% EtOAc in Hexanes over 15 minutes). The solvent gradient was then ramped to 100 % (25% MeOH in EtOAc for 5 minutes). This yielded the title compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.64 (s, 1 H); 8.52-8.48 (m, 2 H); 8.19 (s, 1 H); 7.75 (d, J = 8.0 Hz, 1 H); 7.33 (d, J = 16.6 Hz, 1 H); 7.27 (t, J = 6.7 Hz, 1 H); 7.12-7.08 (m, 2 H); 7.10 (d, J = 15.5 Hz, 1 H); 4.56 (dd, J = 11.3, 6.9 Hz, 1 H); 4.46 (dd, J = 11.3, 7.4 Hz, 1 H); 3.85 (s, 3 H); 2.63 (s, 3 H); 2.14 (dt, J = 8.6, 4.6 Hz, 1 H); 1.98-1.92 (m, 1 H); 1.36 (dt, J = 8.6, 4.9 Hz, 1 H); 1.11 (dt, J = 8.6, 5.1 Hz, 1 H); HRMS m/z (M+H) 375.1815 found, 375.1816 required |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With manganese(II) acetate; copper(ll) bromide In acetonitrile at 40℃; Inert atmosphere; | 34.1; 34.2; 34.3 Example 34 Synthesis of 2- (pyridin-3-yl) -3-diphenylphosphinylpropanenitrile With 3-vinylpyridine and diphenylphosphine oxide as starting materials, the reaction steps are as follows:A solution of 3-vinylpyridine (0.042 g, 0.4 mmol), diphenylphosphine oxide (0.162 g, 0.8(0.279 g, 0.8 mmol), CuBr2 (0.264 g, 0.12 mmol), manganese acetate (0.322 mmol), trimethylcyanosilaneG, 1.2 mmol) and acetonitrile (3 mL) under argon at 40 ° C;TLC tracks the reaction until it ends completely;The crude product obtained after the completion of the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1: 1) to give the desired product(Yield 74%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium 10% on activated carbon; hydrogen; under 760.051 Torr; for 2h; | 2-chloro-5-vinylpyridine (1g, 7.2mmol) is dissolved in 20 ml of methanol; the resulting solution is passed through hydrogen for 2 minutes, after that added 10% Pd/C catalyst (0.1g), subsequently, the mixture is reacted in a hydrogenation reactor (1atm hydrogen) for 2 hours. By LCMS analysis, the reaction mixture is mainly composed of 3-ethylpyridine, 3-vinylpyridine and 2-chloro-5-ethylpyridine composition, and the ratio is roughly 2: 2: 1. These three components are not further separated and purified. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In benzene at 20℃; for 12h; Inert atmosphere; Glovebox; Irradiation; Sealed tube; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With silver tetrafluoroborate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In acetonitrile at 90℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With iron(III) chloride; water; palladium diacetate; triphenylphosphine In 1,4-dioxane at 120℃; for 15h; Sealed tube; Inert atmosphere; Autoclave; regioselective reaction; | |
89 %Chromat. | With iron(II) fluoride; 2C2F3O2(1-)*Pd(2+)*C34H28FeP2; water In toluene at 140℃; for 20h; Sealed tube; | 12 Example 12: Preparation of (2-pyridin-3-yl)propionic acid and 3-(3-pyridyl) propionic acid from 3-vinylpyridine (12) Under a nitrogen atmosphere, catalyst 1 (5 mol%, 2.3 mg) and magnetons were added. Ferrous fluoride (2 mol%, 1.9 mg) and magnetons were added to a 5 mL glass tube. Toluene (2 mL), 3-vinylpyridine (1 mmol, 151 mg), and distilled water (2 mmol, 36 mg) were subsequently added. Place the reaction tube in the reaction kettle, seal the reaction kettle, remove the air in the reaction kettle and wash it with carbon monoxide three times, and finally pressurize the carbon monoxide to 30 bar. After the addition was completed, the reaction kettle was placed in a metal module preheated to 140 degrees Celsius in advance and stirred for 20 hours. After the reaction is completed, the reaction system is cooled to room temperature and the pressure is slowly released. Using dodecane as an internal standard, the yield of 89% was determined by the working curve of gas chromatography, and the branched / straight chain was> 99/1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; water; palladium diacetate; triphenylphosphine In 1,4-dioxane at 120℃; for 15h; Sealed tube; Inert atmosphere; Autoclave; Overall yield = 14 %; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine In N,N-dimethyl-formamide at 110℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; (dimethoxy)methylsilane; copper diacetate; triphenylphosphine In tetrahydrofuran; <i>tert</i>-butyl alcohol at 60℃; for 6h; Inert atmosphere; Sealed tube; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With iodine; tertamethylammonium iodide In water; dimethyl sulfoxide at 30℃; for 5h; | 7.1; 7.2 1) Take 15 mL of borosilicate screw glass tube, according to olefin (mmol):Aqueous solution of Peroxytert-butanol(ml): iodide (mmol): 1:0.3:2, 105 mg of 3-vinylpyridine, 0.3 mL of Peroxytert-butanol(wt 70% aqueous solution),402 mg of tetramethylammonium iodide and 2 mL of solvent dimethyl sulfoxide,Adding a magnet to screw the lid and reacting at 30 ° C for 5 h;2) After the reaction of the above system is completed, 2 mL of a saturated aqueous solution of sodium thiosulfate is added to carry out an iodine reaction, and 10 mL of ethyl acetate and 10 mL of distilled water are added for washing, and the organic phase is separated, and the aqueous phase is extracted with ethyl acetate three times, and organic The phases were dried over anhydrous magnesium sulfate; then, the crude product was obtained by distillation under reduced pressure by rotary evaporation, followed by column chromatography to give 1-iodo-2-peroxy-tert-butyl--3-vinylpyridine. Pure product 276 mg, yield 86%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With C59H52CuN2OP2(1+)*F6P(1-); potassium carbonate In dichloromethane at 40℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium azide; Iodine monochloride In dichloromethane; acetonitrile at -20℃; for 1h; Inert atmosphere; | ||
With iodine(I) azide In acetonitrile at 0℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tris(bipyridine)ruthenium(II) dichloride hexahydrate; potassium carbonate; triphenylphosphine In acetonitrile at 20℃; for 4h; Schlenk technique; Inert atmosphere; Irradiation; | 7 Example 7 In a Schlenk tube equipped with a magnetic stirrer, 163.2 mg of K2CO3 (1.5:1 molar ratio to 3-bromomethylpyridine) and 314.4 mg of triphenylphosphine (with 3-bromomethylpyridine) were added. The molar ratio is 1.5:1), 3.8 mg Ru(bpy)3Cl2-6H2O (molar ratio to 3-bromomethylpyridine is 0.005:1), 60 mg paraformaldehyde, 10 mL acetonitrile, 195 mg 3-bromomethylpyridine The gas was argon gas for 5 minutes, under visible light, at room temperature, and the reaction time was 4 h. The product was separated and purified by petroleum ether-ethyl acetate.The product was obtained as 82 mg of 3-vinylpyridine (formula 7) in a yield of 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.9% | With dihydrogen peroxide; iodine; toluene-4-sulfonic acid; acetophenone In water; acetonitrile at 20℃; for 2h; Inert atmosphere; | 6 Embodiment 6 N2Next, the sealed reactor, adding 105 mg (1 mmol) 3 - vinyl pyridine, 196 mg (1 mmol) 4 - methyl shPs, 101.6 mg (0.4 mmol) I2, 17.2 Mg (0.1 mmol)p- TsOH, 144 mg (1.2 mmol) acetophenone and 8 mLMeCN - H2O (3:1), stirring, then adding 689 mg (6 mmol) 30% of H2O2, Room temperature reaction 2 h, adding 15 ml saturated NaHSO3Solution, stirring 20 min, pressure reducing evaporate MeCN, then adding 10 ml ethyl acetate with 10 mLH2O, layered, ethyl acetate extraction, drying, filtering, the filtrate is concentrated, purified with silica gel column chromatography (petroleum ether/ethyl acetate 20:1), shall (E) -3 - ((4 - Methyl styrene) sulfonyl) pyridine, yield 61.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dihydrogen peroxide In water; acetonitrile at 55℃; for 12h; | 2.4. General procedure for Wacker oxidation of olefins General procedure: With the dissolution of substrate (0.4 mmol) in CH 3 CN (2 mL), Pd0/RGO (0.01 g), H 2 O (0.5 mL), and GO (0.01 g) were orderly added into apressure bottle (35 mL). The mixture was dispersed by ultrasound forabout 30 min at 25 °C. Then H 2 O 2 (30 wt%, 4 mmol) was cautiously added dropwise. Immediately, the reaction system was heated to 55 °Cwith lid closed until the process was fully completed (detected by TLC).Subsequently, Pd0/RGO and GO were removed by centrifuge. Themixture was extracted by deionized water and ethyl acetate. After thelayers were separated, the organic part was washed with deionizedwater, dried with anhydrous NaSO 4 , ltered and evaporated by reducedpressure distillation. Finally, purication of the crude product wascarried out by column chromatography. For 14, 18, 24, 40 (Table 2),excess hydrogen peroxide was added after half of the total reaction time. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With {Au(dppm)}2Cl2; triphenylphosphine In acetonitrile Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In dimethyl sulfoxide at 20℃; for 0.5h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With copper(l) iodide; tert-Butyl peroxybenzoate; potassium hydrogencarbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide; acetone at 40℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With cobalt(II) tetrafluoroborate hexahydrate; N-isopropyl-N,2-dimethylpropan-2-amine In water; acetonitrile at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With bis(1,5-cyclooctadiene)nickel (0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In benzene at 90℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With bis(1,5-cyclooctadiene)nickel (0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 120℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In N,N-dimethyl-formamide at 110℃; Inert atmosphere; | S-20.2 Step 2; Synthesis of (E)-6-(2-(pyridin-3-yl)vinyl)quinoline-4-carboxylic acid. To a solution of 3-vinylpyridine (0.1 g, 0.632 mmol, 1.0 equiv) in DMF (4 rnL) w'as added 6- bromoquinoline-4-carboxy3ic acid (0.159 g, 0.632 mmol, 1.0 equiv), TEA(0.2 ml) and the resulting reaction mixture was purged with N2 gas for 10 min, followed by the addition of Pd.(dppf)Cl2 (0.046 g, 0.063 mmol. 0.1 equiv). The resulting reaction mixture was heated at 110° C for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the mixture was diluted with water solution (20 mL) and washed with ethyl acetate (10 mL x 2). The aqueous layer was separated and freeze dried over yophilizer to obtain (E)-6-(2- (pyridin-3-yl)vinyl)quinoline-4-carboxylic acid (0.200 g, 45 % yield) as an off-white solid. LCMS 277.0 i .M | |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In 1,4-dioxane; water at 120℃; Inert atmosphere; | S-20.1 Step 1 : Synthesis of 3 -vinyl pyridine. To a solution of 3-bromopyridine (0.25 g, 1.582 mmol, 1.0 equiv) in Dioxane ( 10 niL) was added 4, 4,5, 5-tetramethyl-2 -vinyl-1, 3,2- dioxaborolane (0.24 g, 1.582 mmol, 1.0 equiv), Na CCb (0.335 g, 3.164 mmol, 2.0 equiv) in H2O (2 ml) and resulting reaction mixture was purged with N2 gas for 10 min, followed by the addition of Pd(PPh3)2Ch (0.055 g, 0.079 mmol. 0.05 equiv). The resulting reaction mixture was heated at 120° C for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (40 mL c 2). Combined organic extracts were washed with water (10 mL c 4), dried over anhydrous Na2S04 and concentrated. Tire crude product was purified by flash chromatography to 3-vinylpyridine (0.2 g, 40.0 % yield) as a yellow oil. I .('VIS 105.8 I M f I i NMR (400 MHz, DMSO-A) d 8.47 (d, .7=3.07 Hz, 1 H) 7 81 - 7.98 (m, 1 H) 7 38 (dd, / 7.67. 4.60 Hz, 1 H) 6.77 (dd, ./ 1 7.98. 10.96 Hz, 1 H) 5.98 (d, .7=17.98 Hz, 1 H) 5.40 (d. ·/ 10.96 Hz. 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | Stage #1: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.25h; Inert atmosphere; Stage #2: 3-pyridinecarboxaldehyde In tetrahydrofuran at 23℃; for 3.25h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | at 23℃; for 2h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C19H13I2N3O2Ru; hydrogen In isopropyl alcohol at 80℃; for 2h; Autoclave; Schlenk technique; Overall yield = 63 percent; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 5-norbornene-2-carbonitrile; palladium diacetate; caesium carbonate; triphenylphosphine In 1,4-dioxane at 95℃; for 13h; Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With 3,5-difluoro-2,4,6-tris(N-phenylanilino)benzonitrile; potassium <i>tert</i>-butylate In acetonitrile at 20℃; for 20h; Irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With N-hydroxyphthalimide; oxygen; cobalt(II) diacetate tetrahydrate at 20℃; for 48h; | Nicotinaldehyde (2u) 3-Vinylpyridine (21.0 mg, 0.2 mmol), N-hydroxyphthalimide (3.3 mg, 0.02 mmol), Co(OAc)2*4H2O (2.5 mg, 0.01 mmol) were dissolved in HFIP (1.0 mL). The reaction mixture was stirred at room temperature for 48 h under O2. After that time, the reaction mixture was evaporated under vacuum. The crude residue was purified by flash column chromatography to afford (2u) as a clear yellow oil (3.6 mg, yield 17 %) 1H NMR (500 MHz, CDCl3) δ 10.12 (s, 1H), 9.08 (s, 1H), 8.84 (dd, J = 4.8, 1.8 Hz, 1H), 8.17 (d, J = 7.9 Hz, 1H), 7.57-7.43 (m, 1H) ppm; 13C NMR (126 MHz, CDCl3) δ 189.7, 153.7, 151.1, 134.8, 130.4, 123.1 ppm. These data are consistent with those previously reported. [5] |
70 %Chromat. | With oxygen; potassium carbonate In methanol at 130℃; for 12h; Sealed tube; Autoclave; | 22 Example 22 Add Co-N-C (5 mol% relative to the substrate), 3-vinylpyridine (1 mmol), K2CO3 (20 mol%), and 4 mL methanol into a 25 mL polytetrafluoroethylene-lined autoclave, Seal the reactor, fill it with oxygen pressure to 0.4MPa, put the reactor in an oil bath at 130°C, stir and react for 12h at 400 rpm, After the reaction, the reactor was cooled to room temperature, the reactor was opened, and the internal standard biphenyl (60mg) was added. The qualitative products were detected by gas chromatography-mass spectrometry, and the yields of the substrate 3-vinylpyridine and the product 3-pyridinecarboxaldehyde were quantified by gas chromatography internal standard method. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1,2-bis(dimethylphosphanyl)ethane; lithium tert-butoxide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With 1,10-Phenanthroline; silver peroxide; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 40℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With salicylic acid; zinc In acetonitrile at 20℃; for 20h; Sealed tube; | 46 Preparation of compound 2-1: General procedure: Add Zn (327.5 mg, 5 mmol) and benzoic acid (305.3 mg, 2.5 mmol) to the reaction device, then seal the system, evacuate, and introduce bromotrifluoromethane,Then add CH3CN (3mL) and styrene 1-1 (115μL, 1.00mmol) to the reaction system, react at room temperature for 2 hours, and then add 3mL of saturated sodium carbonate aqueous solution,After stirring for 15 min at room temperature, it was filtered, concentrated, and column chromatography was used to obtain 2-1 (146.0 mg, 84% yield) as a pale yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With C100H84CoN8O16; caesium carbonate In toluene at 80℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dmap; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate In dimethyl sulfoxide at 25℃; for 5h; Inert atmosphere; Schlenk technique; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81 %Spectr. | With water-d2; Aspergillus niger ferulic acid decarboxylase In dimethyl sulfoxide at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.2% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine In lithium hydroxide monohydrate; isopropanol at 80℃; for 3h; Inert atmosphere; | 2 3-Vinylpyridine A mixture of 3-iodopyridine (16.0 g, 78.1 mmol, 1.00 eq), potassium trifluoro(vinyl)borate (14.6 g, 109 mmol, 1.40 eq), triethylamine (23.7 g, 234 mmol, 32.6 ml_, 3.00 eq), bis(triphenylphosphine)palladium(ll) dichloride (2.86 g, 3.90 mmol, 0.05 eq) and water (50.0 g, 2.77 mol, 50 ml_, 35.5 eq) in 2-propanol (160 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 80°C for 3 hrs under N2 atmosphere. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (50 mL x 3). The organic layer was washed with brine (50 mL x 2), dried over Na2S04, filtered and concentrated to give the residue. The product was purified by chromatography on a silica gel eluted with petroleum ether: ethyl acetate (from 100: 1 to 2: 1, petroleum ether/ethyl acetate = 5/1, product Rf = 0.4) to give a yellow liquid. 3-Vinylpyridine (3.91 g, 36.8 mmol, 47.2% yield, 99.1% purity) was obtained as a yellow liquid; 1H NMR (400 MHz, CDCI3) d 8.62 (d,1 H), 8.48 (dd, 1 H), 7.73 (dt,1 H), 7.23-7.27 (m, 1 H), 6.71 (dd, 1 H), 5.83 (d, 1 H), 5.38 (d, 1 H). |
47.2% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine In lithium hydroxide monohydrate; isopropanol at 80℃; for 3h; Inert atmosphere; | 2 3-Vinylpyridine A mixture of 3-iodopyridine (16.0 g, 78.1 mmol, 1.00 eq), potassium trifluoro(vinyl)borate (14.6 g, 109 mmol, 1.40 eq), triethylamine (23.7 g, 234 mmol, 32.6 ml_, 3.00 eq), bis(triphenylphosphine)palladium(ll) dichloride (2.86 g, 3.90 mmol, 0.05 eq) and water (50.0 g, 2.77 mol, 50 ml_, 35.5 eq) in 2-propanol (160 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 80°C for 3 hrs under N2 atmosphere. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (50 mL x 3). The organic layer was washed with brine (50 mL x 2), dried over Na2S04, filtered and concentrated to give the residue. The product was purified by chromatography on a silica gel eluted with petroleum ether: ethyl acetate (from 100: 1 to 2: 1, petroleum ether/ethyl acetate = 5/1, product Rf = 0.4) to give a yellow liquid. 3-Vinylpyridine (3.91 g, 36.8 mmol, 47.2% yield, 99.1% purity) was obtained as a yellow liquid; 1H NMR (400 MHz, CDCI3) d 8.62 (d,1 H), 8.48 (dd, 1 H), 7.73 (dt,1 H), 7.23-7.27 (m, 1 H), 6.71 (dd, 1 H), 5.83 (d, 1 H), 5.38 (d, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.41% | In Bicyclo[4.4.0]decane at 250℃; for 1h; Microwave irradiation; | 2 Ethyl 7-(3-pyridyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate To a solution of ethyl 2H- pyridine-1-carboxylate (0.800 g, 5.22 mmol, 2.00 eq) in decalin (5 mL) was added 3- vinylpyridine (274 mg, 2.61 mmol, 1.00 eq). The mixture was stirred at 250°C for 1 hr under microwave irradiation. The reaction mixture was concentrated under reduced pressure to give a residue. The crude product was purified by reversed-phase HPLC (0.1% NhUOH). Ethyl 7-(3-pyridyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate (100 mg, 387 pmol, 7.41% yield) was obtained as a yellow oil; 1H NMR (400 MHz, CDCh) d 8.65-8.43 (m, 2H), 7.57-7.42 (m, 1H), 7.22-7.15 (m, 1H), 6.63-6.57 (m, 1H), 6.32-6.26 (m, 1H), 4.82-4.79 (m, 1H), 4.26- 4.11 (m, 2H), 3.47-3.43 (m, 2H), 3.38-3.35 (m, 1H), 2.92 (s, 1H), 2.22-2.16 (m, 2H), 1.30- 1.24 (m, 3H). |
7.41% | In Bicyclo[4.4.0]decane at 250℃; for 1h; Microwave irradiation; | 2 Ethyl 7-(3-pyridyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate To a solution of ethyl 2H- pyridine-1-carboxylate (0.800 g, 5.22 mmol, 2.00 eq) in decalin (5 mL) was added 3- vinylpyridine (274 mg, 2.61 mmol, 1.00 eq). The mixture was stirred at 250°C for 1 hr under microwave irradiation. The reaction mixture was concentrated under reduced pressure to give a residue. The crude product was purified by reversed-phase HPLC (0.1% NhUOH). Ethyl 7-(3-pyridyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate (100 mg, 387 pmol, 7.41% yield) was obtained as a yellow oil; 1H NMR (400 MHz, CDCh) d 8.65-8.43 (m, 2H), 7.57-7.42 (m, 1H), 7.22-7.15 (m, 1H), 6.63-6.57 (m, 1H), 6.32-6.26 (m, 1H), 4.82-4.79 (m, 1H), 4.26- 4.11 (m, 2H), 3.47-3.43 (m, 2H), 3.38-3.35 (m, 1H), 2.92 (s, 1H), 2.22-2.16 (m, 2H), 1.30- 1.24 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With N-ethyl-N,N-diisopropylamine; cobalt(II) 2,4-pentanedionate In water monomer; acetonitrile at 65℃; for 4h; Inert atmosphere; Schlenk technique; | 3-(tert-Butylperoxy)-1,1,1-trifluoroalkanes 2 and 3-(tert-Butylperoxy)-1-chloro-1,1-difluoroalkanes 4; General Procedure General procedure: To a 50-mL Schlenk flask was added Co(acac)2 (0.1 mmol, 10 mol%). The flask was sealed and evacuated for 30 s and purged with N2 (3 ×). After further evacuating for 30 s, CF3Br (3.1 mmol in a 50-mL Schlenk flask based on our previous report 4g) or CF2ClBr (4.1 mmol, see below) was backfilled. Then the flask was equipped with a N2 balloon and CH3CN (4 mL), alkene (1 mmol), amine (4 mmol, 4 equiv), and TBHP (4 mmol, 4 equiv, 70% solution in H2O) were added sequentially. After stirring for 4 h at 65 °C, the mixture was filtered through a pad of Celite. The filtrate was concentrated, and the residue was purified by chromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; anhydrous sodium carbonate In dimethyl sulfoxide at 25℃; for 5h; Schlenk technique; Glovebox; Irradiation; Sealed tube; |
Tags: 1121-55-7 synthesis path| 1121-55-7 SDS| 1121-55-7 COA| 1121-55-7 purity| 1121-55-7 application| 1121-55-7 NMR| 1121-55-7 COA| 1121-55-7 structure
[ 2682-93-1 ]
3-(2-(Pyridin-4-yl)vinyl)pyridine
Similarity: 0.91
[ 130025-03-5 ]
3-(Pyridin-3-yl)prop-2-en-1-amine
Similarity: 0.85
[ 54356-27-3 ]
(E)-3-(Pyridin-3-yl)acrylonitrile
Similarity: 0.85
[ 2682-93-1 ]
3-(2-(Pyridin-4-yl)vinyl)pyridine
Similarity: 0.91
[ 130025-03-5 ]
3-(Pyridin-3-yl)prop-2-en-1-amine
Similarity: 0.85
[ 54356-27-3 ]
(E)-3-(Pyridin-3-yl)acrylonitrile
Similarity: 0.85
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