* 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.
Reference:
[1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[2] Journal of the Chemical Society, Chemical Communications, 1992, # 8, p. 602 - 604
[3] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
2
[ 1762-42-1 ]
[ 109073-77-0 ]
Yield
Reaction Conditions
Operation in experiment
91%
With sodium tetrahydroborate In ethanol for 3 h; Reflux
Sodium borohydride (1.87g, 49mmol) was added to a suspension of diethyl [2,2'-bipyridine]-4,4'-dicarboxylate 7 (567mg, 1.89mmol) dissolved in absolute ethanol (34mL). The solution was refluxed for 3h. After cooling to room temperature, a saturated ammonium chloride solution (24mL/g of NH4Cl) was added to decompose the excess of sodium borohydride. Ethanol was evaporated under vacuum and the resulting solid was dissolved in a minimum of water using ultrasonic bath. The solution was extracted with ethyl acetate (5×34mL), dried on sodium sulfate and concentrated under vacuum to give a white powder. Yield: 91percent,
89%
With sodium tetrahydroborate In ethanol for 3 h; Reflux
to a suspension of the diester 4 ( 10.0 g, 33.3 mmol) in 300 ml of absolute ethanol was added sodium borohydride (25.19 g, 665.9 mmol) in one portion. The mixture was refluxed for 3 h and cooled to RT, and excess borohydride was decomposed by the dropwise addition saturated ammonium chloride solution (300 ml). Ethanol was removed under vacuum and the precipitated solid was filtered and the solid was dissolved in ethyl acetate (400 ml), washed with water ( 100 ml), dried over anhy. Na2S04and the solvent was removed under vacuum to yield the diol [2,2'-bipyridine]-4,4'-diyldimethanol 5 as awhite powder (5.9 g, 82percent).
88%
With sodium tetrahydroborate In ethanol at 90℃; for 3 h;
Ligand 2(1.02 g, 3.40 mmol) was suspended in 200 proof ethanol (67 mL).Sodium borohydride (2.80 g, 74.0 mmol) was added and the suspension was refluxed at 90 C for 3 h. After cooling, saturated aqueous ammonium chloride (75 mL) was added and ethanol was removed in vacuo. Water was added until all white solid was dissolved.The aqueous layer was extracted with ethyl acetate (450 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed in vacuo to yielda white solid
75%
With sodium tetrahydroborate In ethanol for 3 h; Reflux
To a suspension of compound 4 (6.0 g, 22.0 mmol) in 200 ml of absolute ethanol was added 16.4 g (0.434 mol) of sodium borohydride. The mixture was refluxed for 3 h and cooled to room temperature, and then 200 mL of an ammonium chloride saturated water solution was added to decompose the excess borohydride. The reaction mixture was evaporated to removed the ethanol, and a minimal amount of water was added to dissolve the precipitated solid. The resulting solution was extracted with ethyl acetate (5 × 200 mL), dried overMgSO4, and evaporated to dryness product 5 (3.56 g, 75percent yield).
Reference:
[1] Chemical Communications, 2009, # 48, p. 7545 - 7547
[2] Electrochimica Acta, 2016, vol. 207, p. 313 - 320
[3] Journal of Physical Chemistry B, 1999, vol. 103, # 38, p. 8067 - 8079
[4] Patent: CN105793241, 2016, A, . Location in patent: Paragraph 0129; 0159
[5] Tetrahedron, 2014, vol. 70, # 36, p. 6271 - 6275
[6] Dalton Transactions, 2015, vol. 44, # 12, p. 5577 - 5586
[7] Polyhedron, 2013, vol. 57, p. 52 - 56
[8] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374
[9] Tetrahedron Letters, 2010, vol. 51, # 47, p. 6161 - 6165
[10] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 37 - 46
[11] Inorganic Chemistry, 2015, vol. 54, # 9, p. 4512 - 4519
[12] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[13] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 165, p. 150 - 154
[14] Green Chemistry, 2014, vol. 16, # 9, p. 4179 - 4189
[15] Chemistry - A European Journal, 2017, vol. 23, # 72, p. 18239 - 18251
3
[ 71071-46-0 ]
[ 109073-77-0 ]
Reference:
[1] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 515 - 525
[2] Chemical Communications, 2010, vol. 46, # 13, p. 2256 - 2258
[3] Helvetica Chimica Acta, 2018, vol. 101, # 5,
[4] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[5] Chemical Communications, 2015, vol. 51, # 53, p. 10746 - 10749
[6] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
[7] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[8] Angew. Chem., 2013,
[9] Chemical Communications, 2015, vol. 51, # 27, p. 5840 - 5843
[10] Chemical Communications, 2016, vol. 52, # 46, p. 7398 - 7401
[11] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5919 - 5925
[12] Tetrahedron Letters, 1997, vol. 38, # 25, p. 4389 - 4392
[13] Polymer, 2011, vol. 52, # 15, p. 3318 - 3324
[14] Patent: CN106188151, 2016, A, . Location in patent: Paragraph 0023; 0025; 0029
4
[ 1134-35-6 ]
[ 109073-77-0 ]
Reference:
[1] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5919 - 5925
[2] Heterocycles, 2002, vol. 56, # 1-2, p. 157 - 170
[3] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
[4] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[5] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 37 - 46
[6] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[7] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 515 - 525
[8] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[9] Angew. Chem., 2013,
[10] Green Chemistry, 2014, vol. 16, # 9, p. 4179 - 4189
[11] Chemical Communications, 2015, vol. 51, # 27, p. 5840 - 5843
[12] Chemical Communications, 2016, vol. 52, # 46, p. 7398 - 7401
[13] Tetrahedron, 2014, vol. 70, # 36, p. 6271 - 6275
[14] Chemical Communications, 2015, vol. 51, # 53, p. 10746 - 10749
[15] Dalton Transactions, 2015, vol. 44, # 12, p. 5577 - 5586
[16] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 165, p. 150 - 154
[17] Patent: CN105294773, 2016, A, . Location in patent: Paragraph 0031; 0033
[18] Patent: CN105793241, 2016, A,
[19] Patent: CN106188151, 2016, A,
[20] Chemistry - A European Journal, 2017, vol. 23, # 72, p. 18239 - 18251
[21] Helvetica Chimica Acta, 2018, vol. 101, # 5,
5
[ 6813-38-3 ]
[ 109073-77-0 ]
Reference:
[1] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5919 - 5925
[2] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
[3] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[4] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 37 - 46
[5] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[6] Polymer, 2011, vol. 52, # 15, p. 3318 - 3324
[7] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 515 - 525
[8] Polyhedron, 2013, vol. 57, p. 52 - 56
[9] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[10] Angew. Chem., 2013,
[11] Green Chemistry, 2014, vol. 16, # 9, p. 4179 - 4189
[12] Tetrahedron, 2014, vol. 70, # 36, p. 6271 - 6275
[13] Chemical Communications, 2015, vol. 51, # 53, p. 10746 - 10749
[14] Dalton Transactions, 2015, vol. 44, # 12, p. 5577 - 5586
[15] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 165, p. 150 - 154
[16] Patent: CN105793241, 2016, A,
[17] Chemical Communications, 2016, vol. 52, # 46, p. 7398 - 7401
[18] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374
[19] Patent: CN106188151, 2016, A,
[20] Chemistry - A European Journal, 2017, vol. 23, # 72, p. 18239 - 18251
[21] Helvetica Chimica Acta, 2018, vol. 101, # 5,
6
[ 99970-84-0 ]
[ 109073-77-0 ]
Reference:
[1] European Journal of Inorganic Chemistry, 2001, # 4, p. 1019 - 1029
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[3] Angew. Chem., 2013,
With sodium tetrahydroborate; ethanol; at 90 - 100℃; for 3h;
4,4?-Dimethoxycarbonyl-2,2?-bipyridine (5.9 g) was dissolved in pure EtOH to which sodium borohydride (12 g) was added. The mixture was refluxed for 3 hours at 90-100 C. After cooling to room temperature, saturated NH4C1(aq) was added followed by 300 mE of DDW. The solution was then extracted using ethyl acetate (5x250 mE), driedwith MgSO4, filtered and then concentrated in a vacuum evaporator to obtain the desired solid (4.46 g, 95%). The product was identified using ?H NMR spectroscopy.
With sodium tetrahydroborate; In ethanol; at 80℃; for 3h;
The product obtained from II 630mg was taken and 1g of NaBH4 was added 250mL single-neck flask with stirrer, add 80 mL of the deoxygenated ethanol solution, 80 C under reflux for 3h. Add 20 mL of saturated NH4Cl solution at the end of the reaction. Ethyl acetate and water extraction, retention of ethyl acetate layer, add anhydrous Na2SO4 dry, evaporated solvent, vacuum drying to get white powder.
5-(2-oxo-hexahydro-thieno[3,4-<i>d</i>]imidazol-6-yl)-pentanoic acid 4'-[5-(2-oxo-hexahydro-thieno[3,4-<i>d</i>]imidazol-6-yl)-pentanoyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
60%
The synthesis of the ligand bipy-biotin was done following a modified literature procedure [ 15 ]. The synthesis was performed by addition of 4,4'-dihydroxymethyl-2,2'-bipyridine (0.150?g, 0.69?mmol), 5-[(3aS,4S, 6aR)-2-oxohexahydro-1H-thieno [3,4-d] imidazole-4-yl]pentanoic acid (biotin) (0.424?g, 1.74?mmol) and 4-dimethylaminopyridine (DMAP; 0.085?g; 0.69?mmol) in dimethylformamide (DMF; 10?mL) to a stirred solution and with ice/water bath (0?C). Then N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) was added (0.333?g; 1.735?mmol) to the colorless solution obtained and continue to stir for 30?min with the ice/water bath. After the 30?min, the bath was removed, and the solutions remained stirring all night at room temperature. On the next day the solvent was removed under vacuum and the product washed twice with water and diethyl ether and dried overnight. Yield: 60%; white powder. 1H NMR - [DMSO-d6, Me4Si, delta/ppm]: 8.68 [d, 2, 3JHH?=?4.8, H1], 8.37 [s, 2, H4], 7.43 [d, 2, 3JHH?=?4.8, H2], 6.45 [s, 2, NH], 6.37 [s, 2, NH], 5.25 [s, 4, H6], 4.28 [t, 4, 3JHH?=?6,8, H15], 4.11 [t, 4, 3JHH?=?4, H13), 3.08 (m, 2, H12), 2.80 (dd, 2, 3JHH?=?4.0, 3JHH?=?4.0, H16), 2.57 [d, 2, 3JHH?=?12.4, H16], 2.44 [t, 4, 3JHH?=?7.2, H8], 1.61 [m, 4, H9], 1.48 [m, 4, H11], 1.36 [m, 4, H10]. UV-Vis- [DMSO, lambdamax/nm (epsilon/M-1cm-1)]: 286 (9495). FTIR [KBr, cm-1]: 3385, 3238 (upsilonN-H amine), 3082 (upsilonC-H aromatic), 2935, 2862 (upsilonC-H alkanes), 1732 (upsilonC=O ester), 1705 (upsilonC=O ketone). Elemental analysis calc. for C32H40N6O6S2 (668.83?g/mol): C: 57.47, H: 6.03, N: 12.57, S: 9.59. Found: C: 57.01, H: 6.19, N: 12.47, S: 9.34.
I) oxidation: heating 4, the 4 [...] -dimethyl -2, the 2-dipyridyl [...] 5g with the sample added to the 250 ml shan Kouping, by adding 80 ml of concentrated H2SO4is placed in the water bath under the condition of stirring vigorously, slowly (ensure that temperature will not be violent rise) by adding 17gK2Cr2O7, then put it in 65 C stirring 6h, cooling to room temperature, water filtration, dried to obtain white powder. II) methoxy : taking the resulting product I 2g and 10mLH2SO4, 100mLCH3OH single-mouth bottle with the sample added, 105 C reflux sleepovers, a large amount of water added to the reaction is finished in white flocculent precipitate, by adding NaOH solution to adjust pH of about 9.0, using CH2Cl2a phase extraction, anhydrous Na2SO4drying, turns on lathe solvent to obtain white crystal, yield 88%. III) reduction of ester: heating II the resulting product 630 mg and NaBH41g with the sample added to the 250 ml single-port the bottle, by adding 80 ml of heavy evaporation of ethanol solution, 80 C reflux 3h, reaction into 20 ml saturated NH4Cl solution, ethanol turns on lathe eliminates, by ethyl acetate extraction with water, reserved ethyl acetate layer, adding anhydrous Na2SO4drying, solvent turns on lathe eliminates, vacuum drying to obtain white powder. IV) hydrogen to replace bromate: the intermediate product obtained in III 100 mg, 6m L48% HBr shan Koupingadds to the belt of the sample solution, slowly adding 9 ml concentrated H2SO4, raw material dissolution, the 100 C oil bath stirring pot reflux 6h, end of the reaction, by adding a small amount of water, stirred, adding KOH to adjust pH to 7.0, producing white precipitation, filtration, CH2Cl2dissolved product, without water Na2SO4drying, filtering turns on lathe eliminates solvent, vacuum dried to obtain 4,4 the- [...]two bromine methyl -2, the 2-dipyridyl [...], yield 45%.
4-{2-[2-(4,4'-dimethoxytriphenylmethoxy)ethoxy]ethoxymethyl}-4'-{2-[2-O-<(2-cyanoethoxy)-N,N'-diisopropylaminophosphino]ethoxy>ethoxymethyl}-2,2'-bipyridine[ No CAS ]
(E)-3-(2,5-dimethyl-1H-pyrazol-3-yl)acrylic acid 4'-[(E)-3-(2,5-dimethyl-1H-pyrazol-3-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(S)-2-[(E)-2-(4'-{(E)-3-[(S)-2-(ethoxycarbonyl)cyclopropyl]acryloyloxymethyl}-[2,2']bipyridinyl-4-ylmethyoxycarbonyl)vinyl]cyclopropanecarboxylic acid ethyl ester[ No CAS ]
(E)-3-(5-cyano-6-(methylsulfanyl)pyridin-2-yl)acrylic acid 4'-[(E)-3-(5-cyano-6-(methylsulfanyl)pyridin-2-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(E)-3-((5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxan-2-yl)acrylic acid 4'-[(E)-3-((5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxan-2-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(E)-3-[4-(cyanomethyl(methyl)amino)phenyl]acrylic acid 4'-{(E)-3-[4-(cyanomethyl(methyl)amino)phenyl]acryloyloxymethyl}-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(E)-3-(3,4-dihydro-2H-benzo[b][1,5]dioxepin-7-yl)acrylic acid 4'-[(E)-3-(3,4-dihydro-2H-benzo[b][1,5]dioxepin-7-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(S)-2-[(E)-2-(4'-{(E)-3-[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]acryloyloxymethyl}-[2,2']bipyridinyl-4-ylmethoxycarbonyl)vinyl]pyrrolidine-1-carboxylic acid tert-butyl ester[ No CAS ]
(E)-3-(4-tert-butoxycarbonylaminopyridin-3-yl)acrylic acid 4'-[(E)-3-(4-tert-butoxycarbonylaminopyridin-3-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(E)-3-(6-nitrobenzo[1,3]dioxol-5-yl)acrylic acid 4'-[(E)-3-(6-nitrobenzo[1,3]dioxol-5-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(E)-3-(1-benzenesulfonyl-1H-indol-3-yl)acrylic acid 4'-[(E)-3-(1-benzenesulfonyl-1H-indol-3-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]
(E)-3-[5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)thiophen-2-yl]acrylic acid 4'-{(E)-3-[5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)thiophen-2-yl]acryloyloxymethyl}-[2,2']bipyridinyl-4-ylmethyl ester[ No CAS ]