* 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.
With potassium carbonate In methanol; diethyl ether at 20℃; for 1 h;
2-Ethynyl-4-methylaniline (23) To a stirred solution of 22 (11.32 g, 55.6 mmol) in 2:1 MeOH/Et2O (250 mL) was added K2CO3 (15.38 g, 111 mmol) at room temperature. After stirring for 1 h at this temperature, the reaction mixture was diluted with water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give 23 as a light brown solid without the need for purification (6.79 g, 93percent): 1H NMR (300 MHz, CDCl3) δ 7.14 (d, J=1.5 Hz, 1H), 6.96 (dd, J=8.2, 1.5 Hz, 1H), 6.62 (d, J=8.2 Hz, 1H), 4.11 (s, 2H), 3.36 (s, 1H), 2.21 (s, 3H).
Reference：
[1] Patent: US2014/31559, 2014, A1, . Location in patent: Paragraph 0272
[2] Journal of Organic Chemistry, 2006, vol. 71, # 9, p. 3653 - 3655
[3] Synlett, 2006, # 1, p. 65 - 68
[4] Angewandte Chemie - International Edition, 2007, vol. 46, # 12, p. 2074 - 2077
[5] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4160 - 4165
[6] Organic and Biomolecular Chemistry, 2014, vol. 12, # 9, p. 1387 - 1390
[7] Organic Letters, 2014, vol. 16, # 5, p. 1342 - 1345
[8] Chemical Communications, 2014, vol. 50, # 63, p. 8689 - 8692
[9] Organic and Biomolecular Chemistry, 2016, vol. 14, # 6, p. 2127 - 2133
[10] Synthesis (Germany), 2016, vol. 48, # 6, p. 855 - 864
[11] Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5940 - 5944
[12] Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 10987 - 10999
[13] Organic Letters, 2017, vol. 19, # 13, p. 3402 - 3405
[14] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2720 - 2726
[15] Organic Letters, 2018, vol. 20, # 18, p. 5933 - 5937
3
[ 29289-13-2 ]
[ 215589-37-0 ]
Reference：
[1] Angewandte Chemie - International Edition, 2007, vol. 46, # 12, p. 2074 - 2077
[2] Synlett, 2006, # 1, p. 65 - 68
[3] Journal of Organic Chemistry, 2006, vol. 71, # 9, p. 3653 - 3655
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 9, p. 1387 - 1390
[5] Patent: US2014/31559, 2014, A1,
[6] Organic Letters, 2014, vol. 16, # 5, p. 1342 - 1345
[7] Chemical Communications, 2014, vol. 50, # 63, p. 8689 - 8692
[8] Organic and Biomolecular Chemistry, 2016, vol. 14, # 6, p. 2127 - 2133
[9] Synthesis (Germany), 2016, vol. 48, # 6, p. 855 - 864
[10] Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 5940 - 5944
[11] Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 10987 - 10999
[12] Organic Letters, 2017, vol. 19, # 13, p. 3402 - 3405
[13] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2720 - 2726
[14] Organic Letters, 2018, vol. 20, # 18, p. 5933 - 5937
4
[ 29289-13-2 ]
[ 1066-54-2 ]
[ 215589-37-0 ]
Reference：
[1] Organic Letters, 2012, vol. 14, # 3, p. 836 - 839
[2] Chemistry - A European Journal, 2015, vol. 21, # 20, p. 7413 - 7416
5
[ 106-49-0 ]
[ 215589-37-0 ]
Reference：
[1] Patent: US2014/31559, 2014, A1,
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 6, p. 2127 - 2133
[3] Synthesis (Germany), 2016, vol. 48, # 6, p. 855 - 864
[4] Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 10987 - 10999
[5] Organic Letters, 2017, vol. 19, # 13, p. 3402 - 3405
With potassium carbonate; In methanol; diethyl ether; at 20℃; for 1h;
2-Ethynyl-4-methylaniline (23) To a stirred solution of 22 (11.32 g, 55.6 mmol) in 2:1 MeOH/Et2O (250 mL) was added K2CO3 (15.38 g, 111 mmol) at room temperature. After stirring for 1 h at this temperature, the reaction mixture was diluted with water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give 23 as a light brown solid without the need for purification (6.79 g, 93%): 1H NMR (300 MHz, CDCl3) delta 7.14 (d, J=1.5 Hz, 1H), 6.96 (dd, J=8.2, 1.5 Hz, 1H), 6.62 (d, J=8.2 Hz, 1H), 4.11 (s, 2H), 3.36 (s, 1H), 2.21 (s, 3H).
With Au2(BIPHEP)(NTf2)2; In 1,2-dichloro-ethane; at 25℃; for 6h;Inert atmosphere;
General procedure: In a screw cap vial at 25 C, under an argon atmosphere was charged Au2(BIPHEP)(NTf2)2 (37.2 mg (2.5 mol%). To this was added a freshly prepared solution of 2-ethynylaniline (1a; 117 mg, 1 mmol) in anhydrous 1,2-dichloroethane (1 mL) and stirred at 25 C for 6 h. Then there action mixture was quenched with H2O (5 mL) and extracted with CH2Cl2 (3 × 5 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel) using cyclohexane-EtOAc eluent system to afford the desired dimerization product 2a.
General procedure: The appropriate o-(o-aminophenylethynyl) trifluoroacetanilides 5 and o-(oaminophenylethynyl)anilines 15 were prepared, usually in high yields, via a Sonogashiracross-coupling of 2-iodotrifluoroacetanilides or 2-iodoaniline with 2-ethynylanilines.
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere;
General procedure: Under the protection of nitrogen, a THF solution (20 mL) containing Et3N (15 mmol) and o-ethynylaniline (6 mmol) was added to a flask containing amide (5 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.1 mmol) and CuI (0.05 mmol). The mixture was stirred overnight at room temperature (monitored by TLC). Then the solvent was removed under vacuum. The obtained residue was treated with a mixture of chloroform (30 mL) and water (30 mL). The separated organic layer was washed with brine (15 mL), dried with anhydrous MgSO4. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (EtOAc-PE, 1:2) to give N-[2-[(2-Aminophenyl)ethynyl]phenyl]amide.
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