Name: 4697-62-5|2-Bromo-4,5-dimethoxyphenylacetic acid|97%
Brand: Ambeed
SKU: A275063
Price: 17.0 USD
Availability: InStock
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1
[ 93-40-3 ]
[ 4697-62-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bromine In dichloromethane
95%	With bromine; acetic acid at 20℃; for 3h;	1.1 1) Synthesis of compound (2) Dissolve 72 g of 3,4-dimethoxyphenylacetic acid in 600 mL of glacial acetic acid.After stirring at room temperature for 1 h, 7.2 g of bromine in glacial acetic acid (60 mL) was added and the reaction was continued for 2 h.Add 200mL of ice water, a white precipitate is formed, and filtered.After the filter cake was recrystallized from methanol, 96 g of the compound (2) was obtained.The yield is about 95%.
95%	With bromine; acetic acid at 20℃; for 3h;	1.1 1) Synthesis of compound (2): Dissolve 72 g of 3,4-dimethoxyphenylacetic acid in 600 mL of glacial acetic acid.After stirring at room temperature for 1 h, 7.2 g of bromine in glacial acetic acid (60 mL) was added.After continuing to react for 2 hours, 200 mL of ice water was added and a white precipitate formed.After filtration, the filter cake was recrystallized from methanol to give 96 g of compound (2).The yield is about 95%. Compound (2) is a white solid.

95%	Stage #1: (3,4-Dimethoxyphenyl)acetic acid With acetic acid at 20℃; for 1h; Stage #2: With bromine; acetic acid for 2h;	1.1 Synthesis of compound (2): 72 g of 3,4-dimethoxyphenylacetic acid was dissolved in 600 mL of glacial acetic acid, and stirred at room temperature for 1 hour, then 7.2 g of bromine in glacial acetic acid (60 mL) was added. After the reaction was continued for 2 hours, 200 mL of ice water was added, and white was added. The precipitate formed, filtered, and the cake was recrystallized from methanol to give 96 g of Compound (2).
95%	Stage #1: (3,4-Dimethoxyphenyl)acetic acid With acetic acid at 20℃; for 1h; Stage #2: With bromine; acetic acid at 20℃; for 2h;	1.1 1) Synthesis of Compound (2): After 72g 3,4- dimethoxyphenylacetic acid was dissolved in 600mL of glacial acetic acid was added after stirring at room temperature 1h 7.2g bromine in glacial acetic acid (60 mL) solution, the reaction was continued for 2h, 200mL of ice water, white the resulting precipitate was filtered, the filter cake was recrystallized from methanol to give compound 96g (2), a yield of about 95%.
91%	With bromine In acetic acid at 20℃; for 3h;
91%	With bromine; acetic acid at 0 - 60℃; for 1h; Inert atmosphere;	2-(2-Bromo-4,5-dimethoxyphenyl)acetic acid (9) 2-(3,4-dimethoxyphenyl)acetic acid (5.00 g, 25.5 mmol) was dissolved in glacial acetic acid (10 mL) and cooled to 0 C. Br2(1.31 mL, 25.5 mmol) dissolved in glacial acetic acid (10 mL) was added dropwise. The ice bath was removed, and the reaction was heated at 60 C for 1 h. Upon completion, the reaction mixture was cooled, poured into ice water, and the precipitate was filtered off.This solid was washed with Na2S2O3 (sat., aq.) and H2O to afford the title compound 9 (6.41 g, 23.3 mmol, 91%) as white solid. Rf 0.48(EtOAc); 1H NMR (500 MHz, CDCl3) d 7.04 (s, 1H), 6.79 (s, 1H), 3.86(s, 3H), 3.86 (s, 3H), 3.77 (s, 2H); 13C NMR (126 MHz, CDCl3) d 176.4,149.1, 148.5,125.4, 115.5, 115.2,114.0, 56.3, 56.2, 41.0; IR (nmax/cm1)3550, 1688, 1417, 1281, 1189, 1144, 1045; HRMS (ES) calc. forC10H10O479Br [M H]e 272.9768, found 272.9767; mp 113e114 C.
90%	With sodium hydroxide; bromine In water at 50℃; for 0.5h;
82%	With bromine
80.5%	With bromine In acetic acid for 3h; Ambient temperature;
80%	With bromine In chloroform for 2h;
	With acetic acid durch Bromierung;
	With bromine
	With bromine; sodium acetate 2) 0 deg C, 30 min; Yield given. Multistep reaction;
	With bromine

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]
[2]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109456335, 2019, A Location in patent: Paragraph 0042-0045
[3]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109320534, 2019, A Location in patent: Paragraph 0025; 0028-0030
[4]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109503609, 2019, A Location in patent: Paragraph 0048-0051
[5]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109651413, 2019, A Location in patent: Paragraph 0060-0062
[6]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]
[7]Amaral, Maiara; Anderson, Edward A.; McHugh, Eliza; Pieper, Pauline; Tempone, Andre G. [Tetrahedron, 2019]
[8]Ambros; Von Angerer; Wiegrebe [Archiv der Pharmazie, 1988, vol. 321, # 8, p. 481 - 486]
[9]Song, Xianheng; Luo, Xiang; Sheng, Jianfei; Li, Jianheng; Zhu, Zefeng; Du, Zhibo; Miao, Hui; Yan, Meng; Li, Mingkang; Zou, Yong [RSC Advances, 2019, vol. 9, # 30, p. 17391 - 17398]
[10]Nimgirawath, S.; Srikirin, Y. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 3, p. 272 - 273]
[11]Stenlake; Waigh; Dewar; et al. [European Journal of Medicinal Chemistry, 1981, vol. 16, # 6, p. 515 - 524]
[12]Haworth; Perkin [Journal of the Chemical Society, 1925, vol. 127, p. 1451]
[13]Babor et al. [Chemicke Zvesti, 1954, vol. 8, p. 53,60][Chem.Abstr., 1956, p. 373]
[14]Pandey, G. D.; Tiwari, K. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 2, p. 159]
[15]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

2
[ 51655-39-1 ]
[ 4697-62-5 ]

Reference： [1]Journal of the American Chemical Society,1937,vol. 59,p. 1541,1545
[2]Chemical and Pharmaceutical Bulletin,1974,vol. 22,p. 2108 - 2112

3
[ 4697-62-5 ]
[ 1484-85-1 ]
[ 25829-00-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;	2-(2-Bromo-4,5-dimethoxyphenyl)-N-(3,4-dimethoxyphenethyl)acetamide (7a) General procedure: To a solution of amine 8a (981 mg, 5.41 mmol) and carboxylicacid 9 (1.48 g, 5.41 mmol) in dry DMF (20 mL) was added 1-hydroxybenzotriazole (1.07 g, 7.95 mmol). The reaction mixture was cooled to 0 C, then 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimidehydrochloride (1.30 g, 6.62 mmol) and N-methylmorpholine(2.03 mL,18.0 mmol) were added. The reaction mixturewas warmed slowly to room temperature, and then stirred for 4 h before being quenched by addition of NaHCO3 (10 mL, sat., aq.) and extracted with ethyl acetate (3 10 mL). The combined organiclayers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography over silica gel (2:1 petroleum ether/EtOAc) to give the title compound7a (1.80 g, 4.11 mmol, 76%) as a white solid.
80%	Stage #1: 6-bromohomoveratric acid With thionyl chloride at 76℃; for 1.5h; Stage #2: 3,4-methylenedioxyphenylethylamine In dichloromethane at 20℃; for 4h;	1.2 2) Synthesis of compound (3): 100 g of the compound (2) was dissolved in 100 mL of thionyl chloride, refluxed at 76 ° C for 1.5 h, and the unreacted thionyl chloride was distilled off under reduced pressure to obtain a pale yellow liquid, which was dissolved in 400 mL of dichloromethane. Piperamine and slowly add it to the above pale yellow liquid.Stir at room temperature for 4 hours, distill off dichloromethane under reduced pressure, and recrystallize from methanol to give about 100 g white.A color solid with a yield of about 80%. Compound (3) is a white solid.
80%	Stage #1: 6-bromohomoveratric acid With thionyl chloride at 76℃; for 1.5h; Stage #2: 3,4-methylenedioxyphenylethylamine With thionyl chloride at 20℃; for 4h;	1.2 Synthesis of compound (3): 100 g of the compound (2) was dissolved in 100 mL of thionyl chloride, refluxed at 76 ° C for 1.5 h, and the unreacted thionyl chloride was distilled off under reduced pressure to obtain a pale yellow liquid, which was dissolved in 400 mL of dichloromethane. Ethylamine was added to the above pale yellow liquid, and the mixture was stirred at room temperature for 4 hours, and dichloromethane was evaporated under reduced pressure, and then recrystallized from methanol to give 100 g of white solid.

80%	Stage #1: 6-bromohomoveratric acid With thionyl chloride at 76℃; for 1.5h; Stage #2: 3,4-methylenedioxyphenylethylamine In dichloromethane at 20℃; for 4h;	1.2 2) Synthesis of Compound (3): 100 g of the compound (2) was dissolved in 100 mL of thionyl chloride, refluxed at 76 °C for 1.5 h, and the unreacted thionyl chloride was distilled off under reduced pressure to obtain a pale yellow liquid. 75 g of piperonylamine was dissolved in 400 mL of dichloromethane, and it was slowly added to the above pale yellow liquid, and stirred at room temperature for 4 hours. The dichloromethane was evaporated under reduced pressure and recrystallized from methanol to give about 100 g of white solid. The yield is about 80%.
	at 180℃;

Reference： [1]Amaral, Maiara; Anderson, Edward A.; McHugh, Eliza; Pieper, Pauline; Tempone, Andre G. [Tetrahedron, 2019]
[2]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109320534, 2019, A Location in patent: Paragraph 0025; 0031-0033
[3]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109503609, 2019, A Location in patent: Paragraph 0048; 0052-0054
[4]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109651413, 2019, A Location in patent: Paragraph 0063-0065
[5]Haworth; Perkin [Journal of the Chemical Society, 1925, vol. 127, p. 1451]

4
[ 67-56-1 ]
[ 4697-62-5 ]
[ 4697-57-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuric acid for 0.5h; Reflux;	General procedure for the synthesis of compounds S5a-S5d (UsingS5a as a representative) General procedure: A solution of S4a (5.0 g, 18.18 mmol) and conc. H2SO4 (catalytic) in methanol (50 mL) was refluxed for 30 min. After 30 min, the reaction mixture was cooled to rt and was evaporated under reduced pressure. To the resulting crude water (30 mL) was added, followed by extraction with three portions of 20 mL of dichloromethane. The combined organic layer was dried over Na2SO4, and evaporated under reduced pressure to afford S5a. methyl 2-(2-bromo-4,5-dimethoxyphenyl)acetate (S5a): Brown Oil; (5.19 g, 99 %). methyl 2-(2-bromo-5-methoxyphenyl)acetate (S5b): Brown Oil; (2.09 g,99 %). methyl 2-(2-bromo-4-methoxyphenyl)acetate (S5c): Brown Oil; (2.09 g, 99 %). methyl 2-(2-bromophenyl)acetate (S5d): Clear Oil; (5.27 g, 99 %).
99%	With sulfuric acid Reflux;
80%	With sulfuric acid for 17h; Heating;

Reference： [1]Kapadia, Nirav; Harding, Wayne [Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920]
[2]Čarný, Tomáš; Baudoin, Olivier; Clemenceau, Antonin; Rocaboy, Ronan [Angewandte Chemie - International Edition, 2020, vol. 59, # 43, p. 18980 - 18984][Angew. Chem., 2020, vol. 132, # 43, p. 19142 - 19146,5]
[3]Ambros; Von Angerer; Wiegrebe [Archiv der Pharmazie, 1988, vol. 321, # 8, p. 481 - 486]

5
[ 50-00-0 ]
[ 4697-62-5 ]
[ 16135-41-4 ]

Yield	Reaction Conditions	Operation in experiment
49.7%	With hydrogenchloride; acetic acid at 85 - 90℃; for 24h;

Reference： [1]Nimgirawath, S.; Srikirin, Y. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 3, p. 272 - 273]

6
[ 29456-04-0 ]
[ 4697-62-5 ]
[ 93-40-3 ]
[ 98794-85-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 40%	With potassium <i>tert</i>-butylate In ammonia for 3h; Irradiation;

Reference： [1]Beugelmans, Rene; Ginsburg, Helene [Heterocycles, 1985, vol. 23, # 5, p. 1197 - 1203]

7
[ 51061-22-4 ]
[ 4697-62-5 ]
[ 91421-60-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	In decalin for 2h; Heating;

Reference： [1]Tanaka, Hitoshi; Shibata, Masayoshi; Ito, Kazuo [Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1578 - 1582]

8
[ 4697-62-5 ]
[ 6831-57-8 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In toluene 1.) 30 deg C, 45 min, 2.) reflux, 3 h;
	With thionyl chloride
	With thionyl chloride for 1h; Heating;

	With thionyl chloride In toluene at 135℃;
	With thionyl chloride In benzene Reflux;
	With oxalyl dichloride In dichloromethane at 20℃; for 3.5h; Inert atmosphere;	4.E (2-Bromo-4,5-dimethoxy-phenyl)-acetyl chloride Preparation 4 (2-Bromo-4,5-dimethoxy-phenyl)-acetyl chloride The synthetic procedure used in this preparation is outlined in Scheme E. To a solution of (2-bromo-4,5-dimethoxy-phenyl)-acetic acid (833 mg, 3.03 mmol) in dichloromethane (10 mL) were added oxalyl chloride (0.29 mL, 3.33 mmol) and dimethylformamide (1 drop) under argon atmosphere. The mixture was stirred for 3.5 hours at room temperature, then was concentrated to dryness under reduced pressure. Dichloroethane (15 mL) was added, and resulting solution was back evaporated to dryness to obtain crude (2-bromo-4,5-dimethoxy-phenyl)-acetyl chloride (917 mg).
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3.5h; Inert atmosphere;
	With oxalyl dichloride In dichloromethane
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Inert atmosphere;	1 To a solution of compound 1 (lOg, 36.3 mmol, 1.0 equiv.) in DCM at 0 °C under nitrogen, oxalyl chloride (5.5 g, 43.6 mmol, 1.2 equiv.) and cat. DMF were added in to it. The reaction mixture was allowed to stir at rt. Progress of the reaction was monitored with TLC. After completion of the reaction the reaction mixture was evaporated to dryness, further diluted with DCM and used as such for next reaction. In another RBF, N-Boc-guanidine (7.5 g, 47.2 mmol, 1.3 equiv.) was added and dissolved in DCM. To this solution, DIPEA (7.0 g, 54.4 mmol, 1.5 equiv.) was added at 0 °C under nitrogen. After 30 min. intermediate 2 was added in to it at the same temperature. The reaction mixture was allowed to warm at rt. Progress of the reaction was monitored with TLC. After completion of the reaction, the reaction mixture was washed with sat. aqueous NaHCCb and brine. The organic layer was evaporated to dryness. The crude residue was purified through column chromatography using hexane:EtOAc (80:20) as the eluent to afford compound 3 as light yellow solid (9.5 g, 62.9%); 1HNMR (400 MHz, CDCb) S 1.48 (s, 9H), 3.77 (s, 3H), 3.88 (s, 6H), 6.77 (s, 1H), 6.90 (s, 1H).

Reference： [1]Dominguez, Esther; Lete, Esther; Villa, M. Jesus; Iriondo, Carmen [Heterocycles, 1984, vol. 22, # 5, p. 1217 - 1224]
[2]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]
[3]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]
[4]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]
[5]Location in patent: experimental part Nimgirawath, Surachai; Udomputtimekakul, Phansuang; Taechowisan, Thongchai; Wanbanjob, Asawin; Shen, Yuemao [Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 4, p. 368 - 376]
[6]Current Patent Assignee: ROCHE HOLDING AG - US2010/160387, 2010, A1 Location in patent: Page/Page column 24-25
[7]Lopez-Tapia, Francisco; Walker, Keith A. M.; Brotherton-Pleiss, Christine; Caroon, Joanie; Nitzan, Dov; Lowrie, Lee; Gleason, Shelley; Zhao, Shu-Hai; Berger, Jacob; Cockayne, Debra; Phippard, Deborah; Suttmann, Rebecca; Fitch, William L.; Bourdet, David; Rege, Pankaj; Huang, Xiaojun; Broadbent, Scott; Dvorak, Charles; Zhu, Jiang; Wagner, Paul; Padilla, Fernando; Loe, Brad; Jahangir, Alam; Alker, André [Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8413 - 8426]
[8]Heng, Hui Li; Chee, Chin Fei; Thy, Chun Keng; Tee, Jia Ti; Chin, Sek Peng; Herr, Deron R.; Buckle, Michael J. C.; Paterson, Ian C.; Doughty, Stephen W.; Abd. Rahman, Noorsaadah; Chung, Lip Yong [Chemical Biology and Drug Design, 2019, vol. 93, # 2, p. 132 - 138]
[9]Current Patent Assignee: AVALIV THERAPEUTICS - WO2019/111225, 2019, A1 Location in patent: Paragraph 00350; 00351; 00352; 00353

9
[ 4697-62-5 ]
[ 120-20-7 ]
[ 22185-91-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 2-(2-bromo-4,5-dimethoxyphenyl)acetic acid With 1,1′-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: 2-(3,4-dimethoxyphenyl)-ethylamine In tetrahydrofuran at 0 - 20℃;
80%	at 190 - 210℃; for 2h;
76%	With 4-methyl-morpholine; benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;	2-(2-Bromo-4,5-dimethoxyphenyl)-N-(3,4-dimethoxyphenethyl)acetamide (7a) To a solution of amine 8a (981 mg, 5.41 mmol) and carboxylicacid 9 (1.48 g, 5.41 mmol) in dry DMF (20 mL) was added 1-hydroxybenzotriazole (1.07 g, 7.95 mmol). The reaction mixture was cooled to 0 C, then 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimidehydrochloride (1.30 g, 6.62 mmol) and N-methylmorpholine(2.03 mL,18.0 mmol) were added. The reaction mixturewas warmed slowly to room temperature, and then stirred for 4 h before being quenched by addition of NaHCO3 (10 mL, sat., aq.) and extracted with ethyl acetate (3 10 mL). The combined organiclayers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography over silica gel (2:1 petroleum ether/EtOAc) to give the title compound7a (1.80 g, 4.11 mmol, 76%) as a white solid. Rf 0.8 (2:1 petrolether/EtOAc). 1H NMR (400 MHz, CDCl3) d 6.99 (s, 1H), 6.76 (s, 1H),6.71 (d, J 8.1 Hz, 1H), 6.64 (d, J 2.0 Hz, 1H), 6.58 (dd, J 8.2,2.0 Hz, 1H), 5.44 (br s, 1H), 3.88 (s, 3H), 3.85 (s, 3H), 3.84 (s, 3H), 3.83(s, 3H), 3.59 (s, 2H), 3.46 (app q, J 6.7 Hz, 2H), 2.71 (t, J 6.9 Hz,2H); 13C NMR (101 MHz, CDCl3) d 166.7, 149.0, 148.9, 148.7, 147.6,131.0, 126.5, 120.5, 115.5, 114.7, 113.7, 111.7, 111.2, 56.1, 56.0, 55.8,55.8, 43.6, 40.7, 34.9; IR (nmax/cm1) 3414, 2935, 1633, 1549, 1463,1384, 1244, 1028; HRMS (ES) calc. for C20H24O5N79BrNa [MNa]460.0730, found 460.0729; mp 150e151 C.

Stage #1: 2-(2-bromo-4,5-dimethoxyphenyl)acetic acid With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-(3,4-dimethoxyphenyl)-ethylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 24h;

Reference： [1]Sharma, Vashundhra; Jaiswal, Pradeep K.; Kumar, Surendra; Mathur, Manas; Swami, Ajit K.; Yadav, Dharmendra K.; Chaudhary, Sandeep [ChemMedChem, 2018, vol. 13, # 17, p. 1817 - 1832]
[2]Stenlake; Waigh; Dewar; et al. [European Journal of Medicinal Chemistry, 1981, vol. 16, # 6, p. 515 - 524]
[3]Amaral, Maiara; Anderson, Edward A.; McHugh, Eliza; Pieper, Pauline; Tempone, Andre G. [Tetrahedron, 2019]
[4]Chaudhary, Sandeep; Kumar Shyamlal, Bharti Rajesh; Rahaman T. A, Abdul; Sen, Janmejaya; Tiwari, Mohit K.; Yadav, Lalit [Chemistry - An Asian Journal, 2022]

10
[ 36455-21-7 ]
[ 4697-62-5 ]
[ 32042-14-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2-(2-bromo-4,5-dimethoxyphenyl)acetic acid With 1,1′-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: β-(3-benzyloxy-4-methoxyphenyl)ethylamine In tetrahydrofuran at 0 - 20℃;
	In xylene
	Stage #1: 2-(2-bromo-4,5-dimethoxyphenyl)acetic acid With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: β-(3-benzyloxy-4-methoxyphenyl)ethylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 24h;

Reference： [1]Sharma, Vashundhra; Jaiswal, Pradeep K.; Kumar, Surendra; Mathur, Manas; Swami, Ajit K.; Yadav, Dharmendra K.; Chaudhary, Sandeep [ChemMedChem, 2018, vol. 13, # 17, p. 1817 - 1832]
[2]Ito; Tanaka [Chemical and Pharmaceutical Bulletin, 1974, vol. 22, # 9, p. 2108 - 2112]
[3]Chaudhary, Sandeep; Kumar Shyamlal, Bharti Rajesh; Rahaman T. A, Abdul; Sen, Janmejaya; Tiwari, Mohit K.; Yadav, Lalit [Chemistry - An Asian Journal, 2022]

11
[ 14773-42-3 ]
[ 4697-62-5 ]
[ 65004-82-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	at 180℃; for 3h;

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]

12
[ 4697-62-5 ]
[ 123-11-5 ]
(E)-2-(2-bromo-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)acrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With acetic anhydride; triethylamine at 110℃; for 9h;

Reference： [1]Takeuchi, Kosuke; Ishita, Atsuko; Matsuo, Jun-ichi; Ishibashi, Hiroyuki [Tetrahedron, 2007, vol. 63, # 45, p. 11101 - 11107]

13
[ 4697-62-5 ]
[ 958261-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 57 percent / acetic anhydride; triethylamine / 9 h / 110 °C 2: 75 percent / DBU / acetonitrile / 3 h / 20 °C

Reference： [1]Takeuchi, Kosuke; Ishita, Atsuko; Matsuo, Jun-ichi; Ishibashi, Hiroyuki [Tetrahedron, 2007, vol. 63, # 45, p. 11101 - 11107]

14
[ 93-17-4 ]
[ 4697-62-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 73 percent / NaOH / methanol 2: 95 percent / Br₂ / CH₂Cl₂

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]

15
[ 4697-62-5 ]
2,3,10,11-tetramethoxy-6,7-dihydro-5H-benz[3,4]azepino[1,2-a]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 55 percent / 3 h / 180 °C 2: 62 percent / POCl₃ / acetonitrile / 4 h / Heating 3: 85 percent / t-BuONa; N,N'-bis(2',6'-diisopropylphenyl)dihydroimidazolium*BF₄ / Pd₂(dba)3 / toluene / 80 °C

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]

16
[ 4697-62-5 ]
[ 892804-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 55 percent / 3 h / 180 °C 2: 62 percent / POCl₃ / acetonitrile / 4 h / Heating

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]

17
[ 4697-62-5 ]
[ 41823-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ / 1 h / Heating 2: 6.38 g / aq. Na₂CO₃ / diethyl ether / 6 h / 20 °C 3: 76 percent / POCl₃ / acetonitrile / 4 h / Heating
	Multi-step reaction with 3 steps 1: 80 percent / conc. H₂SO₄ / 17 h / Heating 2: 60 percent / 10 h / 150 - 155 °C 3: POCl₃ / acetonitrile / 4 h / Heating
	Multi-step reaction with 2 steps 1: 80 percent / 2 h / 190 - 210 °C 2: phosphoryl chloride / toluene / 3 h / Heating

	Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C 1.2: 0 - 20 °C 2.1: phosphorus pentachloride / dichloromethane / 13 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane 2: triethylamine / dichloromethane 3: trichlorophosphate / dichloromethane / Reflux
	Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere 2: trifluoromethylsulfonic anhydride; 2-chloropyridine / dichloromethane / 0.25 h / -78 - 0 °C / Inert atmosphere

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]
[2]Ambros; Von Angerer; Wiegrebe [Archiv der Pharmazie, 1988, vol. 321, # 8, p. 481 - 486]
[3]Stenlake; Waigh; Dewar; et al. [European Journal of Medicinal Chemistry, 1981, vol. 16, # 6, p. 515 - 524]
[4]Sharma, Vashundhra; Jaiswal, Pradeep K.; Kumar, Surendra; Mathur, Manas; Swami, Ajit K.; Yadav, Dharmendra K.; Chaudhary, Sandeep [ChemMedChem, 2018, vol. 13, # 17, p. 1817 - 1832]
[5]Heng, Hui Li; Chee, Chin Fei; Thy, Chun Keng; Tee, Jia Ti; Chin, Sek Peng; Herr, Deron R.; Buckle, Michael J. C.; Paterson, Ian C.; Doughty, Stephen W.; Abd. Rahman, Noorsaadah; Chung, Lip Yong [Chemical Biology and Drug Design, 2019, vol. 93, # 2, p. 132 - 138]
[6]Amaral, Maiara; Anderson, Edward A.; McHugh, Eliza; Pieper, Pauline; Tempone, Andre G. [Tetrahedron, 2019]

18
[ 4697-62-5 ]
[ 22185-91-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / 1 h / Heating 2: 6.38 g / aq. Na₂CO₃ / diethyl ether / 6 h / 20 °C
	Multi-step reaction with 2 steps 1: 80 percent / conc. H₂SO₄ / 17 h / Heating 2: 60 percent / 10 h / 150 - 155 °C
	Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane 2: triethylamine / dichloromethane

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]
[2]Ambros; Von Angerer; Wiegrebe [Archiv der Pharmazie, 1988, vol. 321, # 8, p. 481 - 486]
[3]Heng, Hui Li; Chee, Chin Fei; Thy, Chun Keng; Tee, Jia Ti; Chin, Sek Peng; Herr, Deron R.; Buckle, Michael J. C.; Paterson, Ian C.; Doughty, Stephen W.; Abd. Rahman, Noorsaadah; Chung, Lip Yong [Chemical Biology and Drug Design, 2019, vol. 93, # 2, p. 132 - 138]

19
[ 4697-62-5 ]
[ 20975-17-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ / 1 h / Heating 2: 6.38 g / aq. Na₂CO₃ / diethyl ether / 6 h / 20 °C 3: 76 percent / POCl₃ / acetonitrile / 4 h / Heating 4: 85 percent / t-BuONa; N,N'-bis(2',6'-diisopropylphenyl)dihydroimidazolium*BF₄ / Pd₂(dba)3 / toluene / 80 °C
	Multi-step reaction with 5 steps 1: 80 percent / conc. H₂SO₄ / 17 h / Heating 2: 60 percent / 10 h / 150 - 155 °C 3: POCl₃ / acetonitrile / 4 h / Heating 4: NaBH₄ / methanol; H₂O / 2 h / Ambient temperature 5: sodium methylsulfinylmethanide / dimethylsulfoxide / 15 h

Reference： [1]Vincze, Zoltan; Biro, A. Beatrix; Csekei, Marton; Timari, Geza; Kotschy, Andras [Synthesis, 2006, # 8, p. 1375 - 1385]
[2]Ambros; Von Angerer; Wiegrebe [Archiv der Pharmazie, 1988, vol. 321, # 8, p. 481 - 486]

20
[ 4697-62-5 ]
[ 90998-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / toluene / 135 °C 2: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C
	Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 1.) 30 deg C, 45 min, 2.) reflux, 3 h 2: AlCl₃ / CH₂Cl₂ / 3 h / Heating

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]
[2]Dominguez, Esther; Lete, Esther; Villa, M. Jesus; Iriondo, Carmen [Heterocycles, 1984, vol. 22, # 5, p. 1217 - 1224]

21
[ 4697-62-5 ]
[ 90998-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ / toluene / 135 °C 2: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C 4: 16 percent / toluene / 90 °C
	Multi-step reaction with 3 steps 1: thionyl chloride / toluene / 1.) 30 deg C, 45 min, 2.) reflux, 3 h 2: AlCl₃ / CH₂Cl₂ / 3 h / Heating 3: 16 percent / 4 h / 185 - 190 °C
	Multi-step reaction with 3 steps 1: thionyl chloride / toluene / 1.) 30 deg C, 45 min, 2.) reflux, 3 h 2: AlCl₃ / CH₂Cl₂ / 3 h / Heating 3: 14 percent / ammonium formate / 3 h / 185 - 190 °C

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]
[2]Dominguez, Esther; Lete, Esther; Villa, M. Jesus; Iriondo, Carmen [Heterocycles, 1984, vol. 22, # 5, p. 1217 - 1224]
[3]Dominguez, Esther; Lete, Esther; Villa, M. Jesus; Iriondo, Carmen [Heterocycles, 1984, vol. 22, # 5, p. 1217 - 1224]

22
[ 4697-62-5 ]
5-(3,4-dimethoxy-2-hydroxyphenyl)-(3,4-dimethoxyphenyl)pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: SOCl₂ / toluene / 135 °C 2.1: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3.1: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C 4.1: 81 percent / toluene / 90 °C 5.1: 91 percent / Na₂CO₃; HOAc / methanol; H₂O / 145 °C / pH 4 6.1: 81 percent / KOH / methanol; H₂O / 2 h / 70 °C 7.1: n-BuLi / tetrahydrofuran; various solvent(s) / -78 °C 7.2: 44 percent / trimethylborate / tetrahydrofuran; various solvent(s) / -78 - 20 °C

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]

23
[ 4697-62-5 ]
1-phenyl-5,6,9,10-tetramethoxydibenzo[2,3:6,7]oxepino[4,5-d]pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: SOCl₂ / toluene / 135 °C 2: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C 4: 81 percent / toluene / 90 °C 5: 91 percent / Na₂CO₃; HOAc / methanol; H₂O / 145 °C / pH 4 6: 81 percent / KOH / methanol; H₂O / 2 h / 70 °C 7: 74 percent / NaH; CuBr*Me₂S; pyridine / 20 - 120 °C

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]

24
[ 4697-62-5 ]
[ 290353-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: SOCl₂ / toluene / 135 °C 2: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C 4: 81 percent / toluene / 90 °C 5: 91 percent / Na₂CO₃; HOAc / methanol; H₂O / 145 °C / pH 4 6: 81 percent / KOH / methanol; H₂O / 2 h / 70 °C

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]

25
[ 4697-62-5 ]
[ 478316-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: SOCl₂ / toluene / 135 °C 2: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C 4: 81 percent / toluene / 90 °C 5: 91 percent / Na₂CO₃; HOAc / methanol; H₂O / 145 °C / pH 4

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]

26
[ 4697-62-5 ]
[ 478316-37-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ / toluene / 135 °C 2: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]

27
[ 4697-62-5 ]
[ 478316-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ / toluene / 135 °C 2: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C 4: 81 percent / toluene / 90 °C

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]

28
[ 4697-62-5 ]
4-(2-benzoyl-4,5-dimethoxyphenyl)-5-(3,4-dimethoxy-2-hydroxyphenyl)-1-phenylpyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: SOCl₂ / toluene / 135 °C 2.1: 45 percent / AlCl₃ / CH₂Cl₂ / 55 °C 3.1: 88 percent / NaOH; triethylbenzylammonium chloride / tetrahydrofuran / 20 °C 4.1: 81 percent / toluene / 90 °C 5.1: 91 percent / Na₂CO₃; HOAc / methanol; H₂O / 145 °C / pH 4 6.1: n-BuLi / tetrahydrofuran; various solvent(s) / -78 °C 6.2: 56 percent / trimethylborate / tetrahydrofuran; various solvent(s) / -78 - 20 °C

Reference： [1]Olivera, Roberto; SanMartin, Raul; Churruca, Fatima; Dominguez, Esther [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7215 - 7225]

29
[ 4697-62-5 ]
[ 25888-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: SOCl₂ 2.1: 71 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 23 - 27 °C 3.1: POCl₃ / acetonitrile / 2 h / 80 - 83 °C 3.2: 8 percent / NaBH₄ / methanol / 2 h / -78 °C
	Multi-step reaction with 3 steps 1.1: thionyl chloride / 1.5 h / 76 °C 1.2: 4 h / 20 °C 2.1: trichlorophosphate / chloroform / 3 h / Reflux 3.1: sodium tetrahydroborate / methanol / 12 h / 20 °C
	Multi-step reaction with 3 steps 1.1: thionyl chloride / 1.5 h / 76 °C 1.2: 4 h / 20 °C 2.1: trichlorophosphate / chloroform / 3 h / Reflux 3.1: methanol; sodium tetrahydroborate / 12 h / 20 °C

	Multi-step reaction with 3 steps 1.1: thionyl chloride / 1.5 h / 76 °C 1.2: 4 h / 20 °C 2.1: trichlorophosphate / chloroform / 3 h / Reflux 3.1: methanol; sodium tetrahydroborate; hydrogenchloride / water / 12 h / 20 °C
	Multi-step reaction with 3 steps 1.1: thionyl chloride / 1.5 h / 76 °C 1.2: 4 h / 20 °C 2.1: trichlorophosphate / chloroform / 3 h / Reflux 3.1: sodium tetrahydroborate; methanol / 12 h / 20 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]
[2]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109456335, 2019, A
[3]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109320534, 2019, A
[4]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109503609, 2019, A
[5]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109651413, 2019, A

30
[ 4697-62-5 ]
[ 59444-59-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: SOCl₂ 2.1: 68.9 percent / aq. Na₂CO₃ / diethyl ether / 3.5 h / 10 - 15 °C 3.1: 78 percent / BF₃Et₂O; BF₃THF / tetrahydrofuran / 2 h / 70 °C 4.1: 60 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 10 - 15 °C 5.1: POCl₃ / acetonitrile / 5 h / 80 - 83 °C 5.2: 17.2 percent / NaBH₄ / methanol / 1.5 h / -78 °C
	Multi-step reaction with 3 steps 1.1: SOCl₂ 2.1: 66.5 percent / Na₂CO₃ / benzene / 1 h / 80 °C 3.1: POCl₃ / acetonitrile / 1 h / 80 - 82 °C 3.2: 57 percent / NaBH₄ / methanol / 0.5 h / -78 °C
	Multi-step reaction with 3 steps 1.1: SOCl₂ 2.1: 60 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 10 - 15 °C 3.1: POCl₃ / acetonitrile / 5 h / 80 - 83 °C 3.2: 17.2 percent / NaBH₄ / methanol / 1.5 h / -78 °C

	Multi-step reaction with 4 steps 1: 80 percent / conc. H₂SO₄ / 17 h / Heating 2: 60 percent / 10 h / 150 - 155 °C 3: POCl₃ / acetonitrile / 4 h / Heating 4: NaBH₄ / methanol; H₂O / 2 h / Ambient temperature
	Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C 1.2: 0 - 20 °C 2.1: phosphorus pentachloride / dichloromethane / 13 h / 0 - 20 °C 3.1: sodium tetrahydroborate; methanol / 0 - 20 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]
[2]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]
[3]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]
[4]Ambros; Von Angerer; Wiegrebe [Archiv der Pharmazie, 1988, vol. 321, # 8, p. 481 - 486]
[5]Sharma, Vashundhra; Jaiswal, Pradeep K.; Kumar, Surendra; Mathur, Manas; Swami, Ajit K.; Yadav, Dharmendra K.; Chaudhary, Sandeep [ChemMedChem, 2018, vol. 13, # 17, p. 1817 - 1832]

31
[ 4697-62-5 ]
[ 496817-64-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ 2: 68.9 percent / aq. Na₂CO₃ / diethyl ether / 3.5 h / 10 - 15 °C 3: 78 percent / BF₃Et₂O; BF₃THF / tetrahydrofuran / 2 h / 70 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

32
[ 4697-62-5 ]
[ 496817-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ 2: 68.9 percent / aq. Na₂CO₃ / diethyl ether / 3.5 h / 10 - 15 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

33
[ 4697-62-5 ]
5-bromo-1-(2-bromo-4,5-dimethoxybenzyl)-7,8-dimethoxy-3,4-dihydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: SOCl₂ 2.1: 68.9 percent / aq. Na₂CO₃ / diethyl ether / 3.5 h / 10 - 15 °C 3.1: 78 percent / BF₃Et₂O; BF₃THF / tetrahydrofuran / 2 h / 70 °C 4.1: 60 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 10 - 15 °C 5.1: POCl₃ / acetonitrile / 5 h / 80 - 83 °C 5.2: 3.9 percent / NaBH₄ / methanol / 1.5 h / -78 °C
	Multi-step reaction with 3 steps 1.1: SOCl₂ 2.1: 60 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 10 - 15 °C 3.1: POCl₃ / acetonitrile / 5 h / 80 - 83 °C 3.2: 3.9 percent / NaBH₄ / methanol / 1.5 h / -78 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]
[2]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

34
[ 4697-62-5 ]
5-bromo-1-(2-bromo-4,5-dimethoxybenzyl)-7,8-methylenedioxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: SOCl₂ 2.1: 71 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 23 - 27 °C 3.1: POCl₃ / acetonitrile / 2 h / 80 - 83 °C 3.2: 27 percent / NaBH₄ / methanol / 2 h / -78 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

35
[ 4697-62-5 ]
1-(2-bromo-4,5-dimethoxybenzyl)-2-(1-phenylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: SOCl₂ 2.1: 66.5 percent / Na₂CO₃ / benzene / 1 h / 80 °C 3.1: POCl₃ / acetonitrile / 1 h / 80 - 82 °C 3.2: 20 percent / NaBH₄ / methanol / 0.5 h / -78 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

36
[ 4697-62-5 ]
[ 496817-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ 2: 66.5 percent / Na₂CO₃ / benzene / 1 h / 80 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

37
[ 4697-62-5 ]
[ 496817-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ 2: 68.9 percent / aq. Na₂CO₃ / diethyl ether / 3.5 h / 10 - 15 °C 3: 78 percent / BF₃Et₂O; BF₃THF / tetrahydrofuran / 2 h / 70 °C 4: 60 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 10 - 15 °C
	Multi-step reaction with 2 steps 1: SOCl₂ 2: 60 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 10 - 15 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]
[2]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

38
[ 4697-62-5 ]
[ 496817-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ 2: 71 percent / aq. Na₂CO₃ / diethyl ether / 2 h / 23 - 27 °C

Reference： [1]Hashimoto, Naomi; Miyatani, Kumiko; Ohkita, Keiko; Ohishi, Yoshitaka; Kunitomo, Jun-Ichi; Kawasaki, Ikuo; Yamashita, Masayuki; Ohta, Shunsaku [Heterocycles, 2002, vol. 57, # 11, p. 2149 - 2161]

39
[ 4697-62-5 ]
[ 21162-73-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 80 percent / conc. H₂SO₄ / 17 h / Heating 2: 60 percent / 10 h / 150 - 155 °C 3: POCl₃ / acetonitrile / 4 h / Heating 4: NaBH₄ / methanol; H₂O / 2 h / Ambient temperature 5: sodium methylsulfinylmethanide / dimethylsulfoxide / 15 h