Name: 5834-17-3|2-Methoxydibenzo[b,d]furan-3-amine|98%
Brand: Ambeed
SKU: A179221
Rating: 97 (32 reviews)

1
[ 5834-17-3 ]
[ 4535-85-7 ]
N,N-diethyl-N'-(2-methoxy-dibenzofuran-3-yl)-propanediyldiamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 150℃;

Reference： [1]Gilman; Avakian [Journal of the American Chemical Society, 1946, vol. 68, p. 580,582]

2
[ 5834-17-3 ]
[ 104097-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; acetic acid
	Stage #1: 3-amino-2-methoxydibenzofuran With boron tribromide In dichloromethane at 0 - 20℃; for 1h; Stage #2: With water; potassium carbonate In dichloromethane	28 3 - Aminodibenzofuran-2-ol; To a solution of the dibenzofuran (15 g, 70.4 mmol) dissolved in methylene chloride(500 niL) at 00C was added BBr3 (200 niL, 1 M in CH2Cl2) via addition funnel. After the addition was complete, the mixture was allowed to come to room temperature over 1 hour and then quenched with water followed by potassium carbonate (40 g). The resulting solid was recovered by vacuum filtration and dried to afford the hydroxyl dibenzofuran as a white solid (13.2 g, 199 mmol) (M+l, 200).
31.5 g	With boron tribromide In dichloromethane at 0 - 20℃; for 5h;	1.1 Synthesis of Intermediate 1 30.0 g (140.7 mmol) of 2-methoxydibenzofuran-3-amine and 703 mL of dichloromethane were placed in a 3000 mL bite flask and cooled to 0 ° C. Boron tribromide (105.7 g (422.08 mmol)) was diluted to 422 mL of dichloromethane, and boron tribromide (1.0 M DCM solution) was gradually added at 0 ° C. After stirring at 0 ° C. for 1 hour The mixture was stirred at room temperature for 4 hours. After completion of the reaction, the mixture was cooled to 0 ° C., and then 300 mL of distilled water was gradually added. 80.0 g (578.0 mmol) of K2CO3 was dissolved in 289 mL of distilled water, and the mixture was gradually added at 0 ° C. to adjust the pH to 7-8, and then stirred at 0 ° C. for the whole day. The precipitated solid was washed with distilled water, filtered, and dried in a vacuum oven all day long. Gray solid compound (Intermediate) 31.5 g (crude product) was obtained. (The following reaction was carried out without additional purification.)

4.4 g

With boron tribromide In dichloromethane at 0 - 20℃; for 1h;

2.5 Synthesis of H₂L₁, [(Z)-3-((2-hydroxybenzylidene)amino)dibenzo[b,d]furan-2-ol Initially, 3-Amino-dibenzofuran-2-ol was synthesized from 3-amino-2-methoxy-dibenzofuran according to the literature reported method. In brief, 3-amino-2-methoxy-dibenzofuran (5g, 23.5mmol) was dissolved in dry dichloromethane and the temperature was maintained at 0°C to 5°C. Then, boron tribromide (70mL, 1M in CH2Cl2) was added dropwise from a dropping funnel while stirring at ice cold condition. After the addition was complete, the mixture was allowed to come to room temperature over 1h and then quenched with water followed by potassium carbonate (14g). The resulting solid was recovered by vacuum filtration and dried. The hydroxyl dibenzofuran is a white solid (4.4g, 22mmol). In the next step,3-amino-dibenzo[b,d]furan-2-ol (2.0g, 10mmol) was dissolved in 15mL methanol followed by drop wise addition of salicylaldehyde (1.22g, 10.0mmol). Then the mixture was heated to reflux in a water bath and stirred for 6h. This afforded a deep orange colored precipitate of the targeted Schiff base ligand (H2L1). After that the orange solid was filtered and washed with mother liquor, and kept under vacuum.

Reference： [1]Moualim; Venkataraman [Journal Of Scientific and Industrial Research, 1945, vol. 3, p. 447,450][Chem.Abstr., 1945, p. 4606]
[2]Current Patent Assignee: SENHWA BIOSCIENCES - WO2008/131134, 2008, A1 Location in patent: Page/Page column 74
[3]Current Patent Assignee: Samsung Display (in: Samsung); LAPTO CO LTD; SAMSUNG ELECTRONICS CO.,LTD. - JP2021/54811, 2021, A Location in patent: Paragraph 0115-0117
[4]Das, Tapashi; Majumder, Mitali; Rajak, Kajal Krishna; Sepay, Nayim [Journal of Organometallic Chemistry, 2022, vol. 961]

3
[ 5834-17-3 ]
[ 694462-09-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tert.-butylnitrite; copper(I) bromide In acetonitrile at 90℃; for 4h; Inert atmosphere;	1 Example 1-Synthesis of Intermediate 3101 Fill the round bottom flask with raw material 4101 (0.1mol),Tert-butyl nitrite (0.1mol), cuprous bromide (0.12mol), acetonitrile (200ml),The reaction mixture was heated to 90°C under a nitrogen atmosphere and stirred for 4 hours. After the reaction mixture was cooled to room temperature, water was added, followed by extraction with dichloromethane. After the solvent was removed by evaporation, the solid product obtained was slurried with methanol at -20°C. A beige solid was obtained by suction filtration and drying, with a yield of 60%.
	With hydrogenchloride; sodium nitrite anschliessend Erwaermen mit einer aus Kupfer(II)-sulfat, Kaliumbromid, Kaliumdisulfit und wss. Natronlauge bereiteten Loesung und mit wss. Bromwasserstoffsaeure_.;

Reference： [1]Current Patent Assignee: GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO LTD - CN111320613, 2020, A Location in patent: Paragraph 0038-0040
[2]Gilman; Avakian [Journal of the American Chemical Society, 1946, vol. 68, p. 580,582] Moualim; Venkataraman [Journal Of Scientific and Industrial Research, 1945, vol. 3, p. 447,450][Chem.Abstr., 1945, p. 4606]

4
[ 96460-88-7 ]
[ 5834-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; nickel Hydrogenation_.unter Druck;
	With hydrogenchloride; tin(ll) chloride
	With hydrogenchloride; iron

With methanol; nickel at 50 - 100℃; Hydrierung unter Druck;

Reference： [1]Schimmelschmidt [Justus Liebigs Annalen der Chemie, 1950, vol. 566, p. 184,204]
[2]Gilman; Avakian [Journal of the American Chemical Society, 1946, vol. 68, p. 580,582]
[3]Current Patent Assignee: I.G. FARBENINDUSTRIE AG (historic) - DE681640, 1936, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]
[4]Current Patent Assignee: I.G. FARBENINDUSTRIE AG (historic) - DE681640, 1936, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]

5
[ 5834-17-3 ]
[ 100873-38-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite at 90℃; Diazotization;

Reference： [1]Moualim; Venkataraman [Journal Of Scientific and Industrial Research, 1945, vol. 3, p. 447,450][Chem.Abstr., 1945, p. 4606]

6
[ 5834-17-3 ]
[ 533867-45-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 3-amino-2-methoxydibenzofuran With hydrogenchloride; acetic acid; sodium nitrite In water; acetonitrile at 0 - 5℃; Stage #2: With sulfur dioxide; copper dichloride In water; acetonitrile at 20℃; for 16h;

Reference： [1]Ikemoto, Norihiro; Liu, Jinchu; Brands, Karel M.J.; McNamara, James M.; Reider, Paul J. [Tetrahedron, 2003, vol. 59, # 8, p. 1317 - 1325]

7
[ 5834-17-3 ]
[ 17341-93-4 ]
2,2,2-trichloroethyl 2-methoxydibenzo[b,d]furan-3-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyridine In tetrahydrofuran at 0 - 20℃;

Reference： [1]Han, Chong; Porco Jr., John A. [Organic Letters, 2007, vol. 9, # 8, p. 1517 - 1520]

8
[ 5834-17-3 ]
N-(2-methoxydibenzo[b,d]furan-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 89 percent / pyridine / tetrahydrofuran / 0 - 20 °C 2: 81 percent / 4-methyl-2-hydroxyquinoline; Zr(Ot-Bu)4 / chlorobenzene / 0.25 h / 80 °C / microwave irradiation

Reference： [1]Han, Chong; Porco Jr., John A. [Organic Letters, 2007, vol. 9, # 8, p. 1517 - 1520]

9
[ 20357-70-4 ]
[ 5834-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aqueous nitric acid; acetic acid 2: aqueous hydrochloric acid; tin (II)-chloride
	Multi-step reaction with 2 steps 1: aqueous nitric acid; chlorobenzene 2: Raney nickel; ethanol / Hydrogenation_.unter Druck

Reference： [1]Gilman; Avakian [Journal of the American Chemical Society, 1946, vol. 68, p. 580,582]
[2]Schimmelschmidt [Justus Liebigs Annalen der Chemie, 1950, vol. 566, p. 184,204]

10
[ 5834-17-3 ]
[ 149878-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; stannous chloride; sodium nitrite In hydrogenchloride; water	7 Preparation of 2-methoxy-3-dibenzofuranyl hydrazine (chemical intermediate) EXAMPLE 7 Preparation of 2-methoxy-3-dibenzofuranyl hydrazine (chemical intermediate) To 10 g of 3-amino-2-methoxydibenzofuran were added 100 ml of water and 50 ml of concentrated HCl with stirring. The solution was cooled to 0° C. A solution of 3.5 g of sodium nitrite in 15 ml of water was then added dropwise, maintaining a temperature of 0° C. After this addition, the mixture was stirred at 0° C. for one hour. A solution of 40 g of stannous chloride in 50 ml of concentrated HCl cooled to -20° C. was added to the reaction mixture and the mixture was stirred for one hour. The precipitate was then suction filtered and the resulting solid added to a solution of 70 g sodium hydroxide in 500 ml of water cooled in an ice bath. The mixture was then extracted with ether, dried over sodium sulfate for 2 hours, and evaporated to a solid. The solid was washed with hexane, leaving 7 g of 2-methoxy-3-dibenzofuranyl hydrazine of mp 113°-115° C.

Reference： [1]Current Patent Assignee: LANXESS AG - US5367093, 1994, A

11
[ 5834-17-3 ]
[ 369360-49-6 ]
[ 248930-36-1 ]

Yield	Reaction Conditions	Operation in experiment
		179 (2RS,3R)-3-amino-4-cyclohexyl-2-hydroxy-N-(2-methoxydibenzo(b,d)furan-3-yl)butanamide hydrochloride Example 179 (2RS,3R)-3-amino-4-cyclohexyl-2-hydroxy-N-(2-methoxydibenzo(b,d)furan-3-yl)butanamide hydrochloride The product of example 23A and 3-amino-2-methoxydibenzofuran were processed as in example 101 to provide the title compound. MS (APCI) m/e 397 (M+H)+ 1H NMR (300 MHz, MeOH-d4) δ 8.67 (s, 1H), 7.98 (qd, 1H), 7.69 (s, 1H), 7.54 (q, 1H) 7.43 (qd, 1H), 7.43 (dt, 1H), 4.41 (d, 1H), 4.06 (s, 3H), 3.84 (m, 1H), 0.98-1.90 (m, 13H).

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US6242494, 2001, B1

12
[ 5834-17-3 ]
[ 6118-73-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 3-amino-2-methoxydibenzofuran With tert.-butylnitrite; boron trifluoride diethyl etherate In diethyl ether at -20 - 0℃; for 1.41667h; Stage #2: With iodine; sodium iodide In acetonitrile at 20℃; for 1h;
72%	Stage #1: 3-amino-2-methoxydibenzofuran With tert.-butylnitrite; boron trifluoride diethyl etherate In diethyl ether at -20℃; for 1h; Stage #2: With sodium iodide In diethyl ether; acetonitrile at 20℃; for 1h;	1 Synthesis of Intermediate A (0310) 11.1 g (52 mmol) of 3-amino-2-methoxydibenzofuran was dissolved in 130 mL of Et2O in a 1 L round bottomed flask. 26.4 mL (208 mmol) of BF3.Et2O was slowly dropwise added thereto at about -20° C. for about 5 minutes. A mixture of 21.7 mL of tert-butyl nitrile dissolved in 64 mL of Et2O was slowly added to the resulting mixture for 30 minutes, and stirred for 30 minutes. 300 mL of Et2O was added thereto and the resulting mixture was stirred at about 0° C. for 10 minutes. The reaction mixture was concentrated, and a solution of 9.4 g (62.4 mmol) of Nal and 1.2 g (4.7 mmol) of I2 dissolved in 340 mL of dry CH3CN was slowly dropwise added thereto at room temperature for 1 hour. 200 mL of a 20% Na2S2C3 aqueous solution was added thereto, followed by chloroform (300 mL×3), to obtain an organic layer. The organic layer was collected and dried using magnesium sulfate (MgSO4), followed by evaporation to remove the solvent. The resulting residue was separated and purified using silica gel column chromatography to obtain 12.1 g of Intermediate A (Yield: 72%). This compound was identified using liquid chromatography-mass spectroscopy (LC-MS). (0311) LC-MS (m/z)=C13H11NO2 (M+) 213.

Reference： [1]Kawaguchi, Keiko; Nakano, Koji; Nozaki, Kyoko [Organic Letters, 2008, vol. 10, # 6, p. 1199 - 1202]
[2]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; SAMSUNG SDI CO.,LTD. - US2015/336937, 2015, A1 Location in patent: Paragraph 0310; 0311

13
[ 15761-39-4 ]
[ 5834-17-3 ]
[ 1096141-21-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-(tert-butoxycarbonyl)-L-proline With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -5 - 5℃; for 0.5h; Stage #2: 3-amino-2-methoxydibenzofuran In tetrahydrofuran at -5 - 25℃;	1 43.1 g of N-(tert-butoxycarbonyl)-S-proline was dissolved in 500 ml of tetrahydrofuran, and to this were added successively 20.2 g of triethylamine and 21.7 g of ethyl chlorocarbonate. The mixture was stirred at -5 to 5°C for about 30 minutes. To the mixture was added dropwise a tetrahydrofuran solution containing 42.6 g of 3-amino-2-methoxydibenzofuran at the same temperature over about 30 minutes. Then, stirring continued at 15 to 25°C overnight for completion of the reaction. After that, the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The mixture was washed successively with brine, a 5% aqueous solution of sodium bicarbonate and water, and then concentrated in vacuo, to give 86.2 g of (S)-1-(tert-butoxycarbonyl)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide as a solid. 35.0 g of the obtained compound was dissolved in 100 ml of methanol. Under ice-cooling, to this was added 200 ml of 4N-hydrochloric acid/ethyl acetate and then the mixture was stirred overnight. The precipitate was collected by filtration, washed with ethyl acetate and dried, to give 23.4 g of (S)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide hydrochloride as a white crystal. After 10.0 g of the hydrochloride was neutralized by aqueous sodium hydroxide solution, extraction with ethyl acetate, washing with water, concentration and recrystallization from ethyl acetate gave 6.9 g of the free base of the hydrochloride as a white crystal. Melting point: 170 to 171°C Optical rotation: [α]D20 -61.9° (C = 0.5, MeOH) NMR: 1H-NMR (200MHz, CDCl3): δ 1.67-1.88 (2H, m), 2.01-2.30 (1H, m), 2.98-3.19 (2H, m), 3.90-3.98 (1H, m), 4.01 (3H, S), 7.26-7.43 (4H, m), 7.52-7.56 (1H, m), 7.82-7.86 (1H, m), 8.79 (1H, S)

Reference： [1]Current Patent Assignee: HAMARI CHEMICALS LTD - EP2172443, 2010, A1 Location in patent: Page/Page column 11

14
[ 5834-17-3 ]
[ 1096141-21-7 ]
(S)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (S)-1-(tert-butoxycarbonyl)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide With hydrogenchloride In ethyl acetate Stage #2: 3-amino-2-methoxydibenzofuran In tetrahydrofuran at -5 - 25℃;	1 43.1 g of N-(tert-butoxycarbonyl)-S-proline was dissolved in 500 ml of tetrahydrofuran, and to this were added successively 20.2 g of triethylamine and 21.7 g of ethyl chlorocarbonate. The mixture was stirred at -5 to 5°C for about 30 minutes. To the mixture was added dropwise a tetrahydrofuran solution containing 42.6 g of 3-amino-2-methoxydibenzofuran at the same temperature over about 30 minutes. Then, stirring continued at 15 to 25°C overnight for completion of the reaction. After that, the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The mixture was washed successively with brine, a 5% aqueous solution of sodium bicarbonate and water, and then concentrated in vacuo, to give 86.2 g of (S)-1-(tert-butoxycarbonyl)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide as a solid. 35.0 g of the obtained compound was dissolved in 100 ml of methanol. Under ice-cooling, to this was added 200 ml of 4N-hydrochloric acid/ethyl acetate and then the mixture was stirred overnight. The precipitate was collected by filtration, washed with ethyl acetate and dried, to give 23.4 g of (S)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide hydrochloride as a white crystal. After 10.0 g of the hydrochloride was neutralized by aqueous sodium hydroxide solution, extraction with ethyl acetate, washing with water, concentration and recrystallization from ethyl acetate gave 6.9 g of the free base of the hydrochloride as a white crystal. Melting point: 170 to 171°C Optical rotation: [α]D20 -61.9° (C = 0.5, MeOH) NMR: 1H-NMR (200MHz, CDCl3): δ 1.67-1.88 (2H, m), 2.01-2.30 (1H, m), 2.98-3.19 (2H, m), 3.90-3.98 (1H, m), 4.01 (3H, S), 7.26-7.43 (4H, m), 7.52-7.56 (1H, m), 7.82-7.86 (1H, m), 8.79 (1H, S)

Reference： [1]Current Patent Assignee: HAMARI CHEMICALS LTD - EP2172443, 2010, A1 Location in patent: Page/Page column 11

15
[ 5834-17-3 ]
(S)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide hydrochloride [ No CAS ]
[ 1096141-19-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (S)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide hydrochloride With sodium hydroxide In water Stage #2: 3-amino-2-methoxydibenzofuran In tetrahydrofuran at -5 - 25℃;	1 43.1 g of N-(tert-butoxycarbonyl)-S-proline was dissolved in 500 ml of tetrahydrofuran, and to this were added successively 20.2 g of triethylamine and 21.7 g of ethyl chlorocarbonate. The mixture was stirred at -5 to 5°C for about 30 minutes. To the mixture was added dropwise a tetrahydrofuran solution containing 42.6 g of 3-amino-2-methoxydibenzofuran at the same temperature over about 30 minutes. Then, stirring continued at 15 to 25°C overnight for completion of the reaction. After that, the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The mixture was washed successively with brine, a 5% aqueous solution of sodium bicarbonate and water, and then concentrated in vacuo, to give 86.2 g of (S)-1-(tert-butoxycarbonyl)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide as a solid. 35.0 g of the obtained compound was dissolved in 100 ml of methanol. Under ice-cooling, to this was added 200 ml of 4N-hydrochloric acid/ethyl acetate and then the mixture was stirred overnight. The precipitate was collected by filtration, washed with ethyl acetate and dried, to give 23.4 g of (S)-N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamide hydrochloride as a white crystal. After 10.0 g of the hydrochloride was neutralized by aqueous sodium hydroxide solution, extraction with ethyl acetate, washing with water, concentration and recrystallization from ethyl acetate gave 6.9 g of the free base of the hydrochloride as a white crystal. Melting point: 170 to 171°C Optical rotation: [α]D20 -61.9° (C = 0.5, MeOH) NMR: 1H-NMR (200MHz, CDCl3): δ 1.67-1.88 (2H, m), 2.01-2.30 (1H, m), 2.98-3.19 (2H, m), 3.90-3.98 (1H, m), 4.01 (3H, S), 7.26-7.43 (4H, m), 7.52-7.56 (1H, m), 7.82-7.86 (1H, m), 8.79 (1H, S)

Reference： [1]Current Patent Assignee: HAMARI CHEMICALS LTD - EP2172443, 2010, A1 Location in patent: Page/Page column 11

16
[ 5834-17-3 ]
[ 6160-65-2 ]
(2-methoxy-dibenzofuran-3-yl)-thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: 3-amino-2-methoxydibenzofuran; 1,1'-Thiocarbonyldiimidazole In dichloromethane at 20℃; for 3h; Stage #2: With ammonia; water In dichloromethane at 20℃;

Reference： [1]Location in patent: experimental part Kang, Iou-Jiun; Wang, Li-Wen; Yeh, Teng-Kuang; Lee, Chung-Chi; Lee, Yen-Chun; Hsu, Sheng-Ju; Wu, Yen-Shian; Wang, Jing-Chyi; Chao, Yu-Sheng; Yueh, Andrew; Chern, Jyh-Haur [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6414 - 6421]

17
[ 5834-17-3 ]
[ 32315-10-9 ]
[ 1263096-87-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
	With triethylamine In dichloromethane at 20℃; for 25h; Cooling with ice;

Reference： [1]Biedermann, Frank; Rauwald, Urs; Cziferszky, Monika; Williams, Kyle A.; Gann, Lauren D.; Guo, Bi Y.; Urbach, Adam R.; Bielawski, Christopher W.; Scherman, Oren A. [Chemistry - A European Journal, 2010, vol. 16, # 46, p. 13716 - 13722]
[2]Location in patent: experimental part Biedermann, Frank; Appel, Eric A.; Del Barrio, Jesus; Gruendling, Till; Barner-Kowollik, Christopher; Scherman, Oren A. [Macromolecules, 2011, vol. 44, # 12, p. 4828 - 4835]

18
[ 5834-17-3 ]
[ 1256749-70-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 2.1: triethylamine / chloroform / 0.33 h / 20 °C / Inert atmosphere 2.2: 120 h / Reflux; Inert atmosphere

Reference： [1]Venkatachalam; Barreto, Jose; Kreher, Ute; Reutens, David C.; Spiccia, Leone [Inorganica Chimica Acta, 2010, vol. 363, # 12, p. 2896 - 2904]

19
[ 5834-17-3 ]
[ 1256749-72-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetonitrile / 0.17 h / Inert atmosphere 2.2: 96 h / 20 °C / Reflux
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 2: potassium carbonate; potassium iodide / acetonitrile / 4 h / Reflux; Inert atmosphere

Reference： [1]Venkatachalam; Barreto, Jose; Kreher, Ute; Reutens, David C.; Spiccia, Leone [Inorganica Chimica Acta, 2010, vol. 363, # 12, p. 2896 - 2904]
[2]Barreto, José; Joshi, Tanmaya; Venkatachalam; Reutens, David C.; Graham, Bim; Spiccia, Leone [Journal of Coordination Chemistry, 2015, vol. 68, # 2, p. 335 - 349]

20
[ 5834-17-3 ]
[ 1256749-71-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetonitrile / 0.17 h / Inert atmosphere 2.2: 96 h / 20 °C / Reflux 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 2: potassium carbonate; potassium iodide / acetonitrile / 4 h / Reflux; Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere

Reference： [1]Venkatachalam; Barreto, Jose; Kreher, Ute; Reutens, David C.; Spiccia, Leone [Inorganica Chimica Acta, 2010, vol. 363, # 12, p. 2896 - 2904]
[2]Barreto, José; Joshi, Tanmaya; Venkatachalam; Reutens, David C.; Graham, Bim; Spiccia, Leone [Journal of Coordination Chemistry, 2015, vol. 68, # 2, p. 335 - 349]

21
[ 5834-17-3 ]
[ 79-04-9 ]
[ 379726-31-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;
	With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;
	With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h;

With triethylamine In tetrahydrofuran at 20℃; for 1h; Cooling with ice;

2.1.1. Synthesis of 2-chloro-N-(2-methoxydibenzofuran-3-yl)acetamide (1) 2-Methoxydibenzofuran-3-amine (40 mmol, 8.52 g) wasdissolved in tetrahydrofuran (100 mL) and triethylamine (41mmol, 3.483 g) was added to it. The solution was cooled inan ice bath and chloroacetyl chloride (41 mmol, 3.88 g) wasadded dropwise with constant stirring. After the drippingwas over, the reaction mixture was stirred for additional 1hat room temperature. Then, the solvent was evaporated underreduced pressure, raw product was washed with water, driedand recrystallized from ethanol.

Reference： [1]Location in patent: experimental part Venkatachalam; Barreto, Jose; Kreher, Ute; Reutens, David C.; Spiccia, Leone [Inorganica Chimica Acta, 2010, vol. 363, # 12, p. 2896 - 2904]
[2]Barreto, José; Joshi, Tanmaya; Venkatachalam; Reutens, David C.; Graham, Bim; Spiccia, Leone [Journal of Coordination Chemistry, 2015, vol. 68, # 2, p. 335 - 349]
[3]Yurttaş, Leyla; Abu Mohsen, Usama; Ozkan, Yeşim; Cobanoglu, Simla; Levent, Serkan; Kaplancikli, Zafer Asım [Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, # 6, p. 1177 - 1183]
[4]Yurttaş, Leyla; Çavuşoğlu, Betül Kaya; Temel, Halide Edip; Çiftçi, Gülşen Akalın [Letters in drug design and discovery, 2021, vol. 18, # 5, p. 471 - 479]

22
[ 497931-76-7 ]
[ 5834-17-3 ]
[ 1256353-10-2 ]