* 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] Tetrahedron Letters, 1988, vol. 29, # 35, p. 4427 - 4430
[2] Synlett, 2005, # 13, p. 2043 - 2046
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 18, p. 5590 - 5602
[4] Organic Process Research and Development, 2000, vol. 4, # 6, p. 460 - 466
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5293 - 5300
[6] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5720 - 5733
[7] Journal of the American Chemical Society, 2017, vol. 139, # 51, p. 18522 - 18535
[8] Journal of the Chemical Society, 1942, p. 689
[9] Journal of the Chemical Society, 1949, p. 1855,1862[10] Journal of the Chemical Society, 1946, p. 676,679
[11] Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 3300 - 3313
[12] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2891 - 2898
[13] Australian Journal of Chemistry, 1998, vol. 51, # 5, p. 389 - 396
[14] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1971, vol. 19, p. 219 - 225
2
[ 575-44-0 ]
[ 74-88-4 ]
[ 3900-49-0 ]
Yield
Reaction Conditions
Operation in experiment
90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h;
Into a round-bottom flask equipped with a stirring apparatus, 1.6 g (10.0 mmol) of 1,6-dihydroxynaphthalene (Compound 39: produced by Tokyo Chemical Industry Co., Ltd.), and 15 mL of N,N-dimethylformamide (DMF) were added for dissolution, and thrther 14.2 g (100.0 mmol) of methyl iodide (produced by Wako Pure Chemical Industries, Ltd.), and 13.8 g (100.0 mmol) of potassium carbonate (produced by Wako Pure Chemical Industries, Ltd.) were added, and the reaction was carried out at room temperature for 2 hours. Afier completion of the reaction, dichloromethane and water were added, and then an organic layer, obtained by solution separation, was washed with water, and the solvent was removed from the reaction solution by concentration under reduced pressure to obtain 1 .7 g (yield:90percent) of a colorless liquid methyl derivative (Compound40).
Reference：
[1] Organic Process Research and Development, 2009, vol. 13, # 3, p. 647 - 651
[2] Synlett, 2005, # 13, p. 2043 - 2046
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 18, p. 5590 - 5602
[4] Journal of the American Chemical Society, 2017, vol. 139, # 51, p. 18522 - 18535
[5] Journal of the Chemical Society, 1949, p. 1855,1862[6] Journal of the Chemical Society, 1946, p. 676,679
[7] Journal fuer Praktische Chemie (Leipzig), 1916, vol. <2> 94, p. 3
[8] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2891 - 2898
[9] Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5252 - 5258
[10] Australian Journal of Chemistry, 1998, vol. 51, # 5, p. 389 - 396
[11] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5293 - 5300
[12] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5720 - 5733
4
[ 67-56-1 ]
[ 3900-49-0 ]
Reference：
[1] Chemical Communications, 2014, vol. 50, # 47, p. 6243 - 6245
5
[ 32940-13-9 ]
[ 3900-49-0 ]
Reference：
[1] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1971, vol. 19, p. 219 - 225
6
[ 67-56-1 ]
[ 575-44-0 ]
[ 3900-49-0 ]
[ 22604-07-5 ]
[ 150712-57-5 ]
Reference：
[1] Australian Journal of Chemistry, 1993, vol. 46, # 5, p. 731 - 737
7
[ 3900-49-0 ]
[ 4018-91-1 ]
Reference：
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2891 - 2898
Butyllithium (2.5 M solution in hexanes, 10.1 mL, 26.5 mmol) was added dropwise to a cooled (-78 C) stirred solution of <strong>[3900-49-0]1,6-dimethoxynaphthalene</strong> (5.00 g, 26.5 mmol) in anhydrous THF (50 mL) under an argon atmosphere. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature for 12-14 h. The mixture was again cooled (-78 C) and iodine (6.74 g, 26.5 mmol) in anhydrous THF (50 mL) was added dropwise over 1 h. The reaction mixture was brought to room temperature and quenched with satd NH4Cl (10 mL) and satd Na2S2O3 (15 mL). The mixture was concentrated in vacuo and the organic dissolved in diethyl ether (200 mL), washed with water (3*50 mL), dried (MgSO4) and concentrated in vacuo to approximately 50 mL. The concentrated solution was filtered through a Celite/silica plug eluting with diethyl ether and the filtrate concentrated in vacuo to yield a colourless solid (6.37 g, 76%), which was recrystallized from MeOH to afford the title compound as off white prisms, mp 110-112 C (lit. 15 mp 110.5-112 C). 1H NMR (300 MHz, CDCl3) delta 8.72 (s, 1H), 7.45-7.28 (m, 2H), 7.01 (s, 1H), 6.72-6.54 (d, J=7.6 Hz, 1H) 3.95 (s, 6H). 13C NMR (75 MHz, CDCl3): delta 155.6, 154.6, 135.6, 134.0, 127.3, 122.2, 119.0, 105.3, 102.5, 86.8, 56.3, 55.5. IR (ATR) (cm-1) 2959, 2928, 2836, 1576, 1447, 1424, 1385, 1359. HRMS (EI+, 70 eV) m/z: [M]+ calcd for C12H11O2I 313.9798, found 313.9794. Anal. Calcd for C12H11O2I: C, 45.88; H, 3.53; I, 40.40. Found: C, 46.04; H, 3.26; I, 39.99.
2,4-Dihydroxybenzophenone (2.0 g, 9.3 mmol) was dissolved in THF(100 ml_). The solution was cooled to -780C in a dry ice bath. n-BuLi (1 1.6 ml_, 1.6 M in hexane) was added drop-wise with constant stirring. The mixture was allowed to warm to room temperature overnight, and then cooled to 0 0C in an ice bath. Then t- butyldimethylsilyl chloride (2.9 g, 19.5 mmol) in THF (20 mL) was added drop-wise. After the addition was complete, the solution was allowed to warm to room temperature over 4 hours. The solution was cooled to -780C, and a solution of lithiated 1 ,6-dimethoxynaphthalene (1.84 g, 9.8 mmol) was added drop-wise. The solution was then allowed to warm to room temperature overnight. HCI (10 mL, 4 M) was added in a single portion. The solution was stirred at room temperature for 30 min. Deionized H2O (200 mL) was added. Most of the THF was then removed under vacuum. The remaining aqueous material was extracted with CH2CI2 and dried over MgSO4. Purification by flash chromatography (EtOAc) produced 56 mg (1.7 % yield, based on 2,4-dihydroxybenzophenone) of SNAFR-1 methyl ether, Compound 18. Then 18 mg of Compound 18 was dissolved in anhydrous CH2CI2. The solution was cooled in a dry ice bath. Then 0.3 mL BBr3 was added to demethylate Compound 18 to obtain 14 mg (81 % yield) of SNAFR-1.
When a solution of lithiated Compound 9 was reacted with methyl benzoate, we obtained Compounds 10 and 11 in yields of 71 % and 12%, respectively. When phthalic anhydride was used in place of methylbenzoate, Compound 12 was obtained in 55% yield. When lithiated 1 ,6-dimethoxynaphthalene was reacted with Compound 2, 4-dimethoxybenzophenone, Compounds 13 and 14 were isolated in 1 1 % and 71 % yields, respectively. Trace amounts of Compound 15 were also produced, presumably due to trace amounts of 2-hydroxy-4- methoxybenzophenone in the reaction mixture from incomplete methylation of 2,4- dihydroxybenzophenone. Single crystal X-ray structure analysis confirmed the assigned structures of Compounds 10-15.
When a solution of lithiated Compound 9 was reacted with methyl benzoate, we obtained Compounds 10 and 11 in yields of 71 % and 12%, respectively. When phthalic anhydride was used in place of methylbenzoate, Compound 12 was obtained in 55% yield. When lithiated 1 ,6-dimethoxynaphthalene was reacted with Compound 2, 4-dimethoxybenzophenone, Compounds 13 and 14 were isolated in 1 1 % and 71 % yields, respectively. Trace amounts of Compound 15 were also produced, presumably due to trace amounts of 2-hydroxy-4- methoxybenzophenone in the reaction mixture from incomplete methylation of 2,4- dihydroxybenzophenone. Single crystal X-ray structure analysis confirmed the assigned structures of Compounds 10-15.
When a solution of lithiated Compound 9 was reacted with methyl benzoate, we obtained Compounds 10 and 11 in yields of 71 % and 12%, respectively. When phthalic anhydride was used in place of methylbenzoate, Compound 12 was obtained in 55% yield. When lithiated 1 ,6-dimethoxynaphthalene was reacted with Compound 2, 4-dimethoxybenzophenone, Compounds 13 and 14 were isolated in 1 1 % and 71 % yields, respectively. Trace amounts of Compound 15 were also produced, presumably due to trace amounts of 2-hydroxy-4- methoxybenzophenone in the reaction mixture from incomplete methylation of 2,4- dihydroxybenzophenone. Single crystal X-ray structure analysis confirmed the assigned structures of Compounds 10-15.
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;
Into a round-bottom flask equipped with a stirring apparatus, 1.6 g (10.0 mmol) of <strong>[575-44-0]1,6-dihydroxynaphthalene</strong> (Compound 39: produced by Tokyo Chemical Industry Co., Ltd.), and 15 mL of N,N-dimethylformamide (DMF) were added for dissolution, and thrther 14.2 g (100.0 mmol) of methyl iodide (produced by Wako Pure Chemical Industries, Ltd.), and 13.8 g (100.0 mmol) of potassium carbonate (produced by Wako Pure Chemical Industries, Ltd.) were added, and the reaction was carried out at room temperature for 2 hours. Afier completion of the reaction, dichloromethane and water were added, and then an organic layer, obtained by solution separation, was washed with water, and the solvent was removed from the reaction solution by concentration under reduced pressure to obtain 1 .7 g (yield:90%) of a colorless liquid methyl derivative (Compound40).
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