[ CAS No. 1951-26-4 ] {[proInfo.proName]}

Name: 1951-26-4|(2-Butylbenzofuran-3-yl)(4-hydroxy-3,5-diiodophenyl)methanone|98%
Brand: Ambeed
SKU: A855276
Rating: 96 (22 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 1951-26-4 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 1951-26-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1951-26-4 ]

SDS Specification

Alternatived Products of [ 1951-26-4 ]

Product Details of [ 1951-26-4 ]

CAS No. :	1951-26-4	MDL No. :	MFCD02675787
Formula :	C₁₉H₁₆I₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PNFMEGSMKIHDFZ-UHFFFAOYSA-N
M.W :	546.14	Pubchem ID :	74769
Synonyms :		Chemical Name :	(2-Butylbenzofuran-3-yl)(4-hydroxy-3,5-diiodophenyl)methanone

Safety of [ 1951-26-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1951-26-4 ]

* 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.

Upstream synthesis route of [ 1951-26-4 ]
Downstream synthetic route of [ 1951-26-4 ]

[ 1951-26-4 ] Synthesis Path-Upstream 1~1

1
[ 869-24-9 ]
[ 1951-26-4 ]
[ 19774-82-4 ]

Yield	Reaction Conditions	Operation in experiment
87.6%	With potassium carbonate In water; toluene for 4 h;	130.0 g (0.238 mol) of the compound of formula 7 and 43.4 g (0.2523 mol) of 2-chloro-N,N-diethylethanamine hydrochloride,98.9g (0.7164mol) of potassium carbonate, 208g of water, and 495g of toluene were mixed, mechanically stirred, and the reaction was heated for 4 hours.Let stand, layer, wash the organic phase 2 times, adjust the pH of the organic phase with HCl to 1-2, -0.09 to -0.08 MPa/40-65°C, and distill off the solvent.The crude amiodarone hydrochloride of Formula 1 was obtained in an amount of 162.4 g in a yield of 100percent (based on the compound represented by Formula 7).Take 50g crude amiodarone, dissolve it in 100g dichloromethane, pass the silica gel (400g) column,The column was flushed with a mixture of 450 g of dichloromethane and 70 g of methanol containing the amiodarone hydrochloride effluent.Evaporation of the solvent gave amiodarone hydrochloride 45 g of a refined product, which was refined by refluxing with 450 g of acetone and dried to obtain 43.8 g of amiodarone hydrochloride with a refined yield of 87.6percent.

Reference： [1] Patent: CN107382925, 2017, A, . Location in patent: Paragraph 0098-0100

[ 1951-26-4 ] Synthesis Path-Downstream 1~51

1
[ 105-36-2 ]
[ 1951-26-4 ]
[4-(2-butylbenzofuran-3-carbonyl)-2,6-diiodophenoxy]acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone at 50℃; for 24h;

Reference： [1]Waldhauser, Katri Maria; Toeroek, Michael; Ha, Huy-Riem; Thomet, Urs; Konrad, Daniel; Brecht, Karin; Follath, Ferenc; Kraehenbuehl, Stephan [Journal of Pharmacology and Experimental Therapeutics, 2006, vol. 319, # 3, p. 1413 - 1423]
[2]Carlsson, Bo; Singh; Temciuc, Marcel; Nilsson, Stefan; Li, Yi-Lin; Mellin, Charlotta; Malm, Johan [Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 623 - 630]

2
[ 75-03-6 ]
[ 1951-26-4 ]
(2-butylbenzofuran-3-yl)-[4-ethoxy-3,5-diiodophenyl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In acetone at 50℃; for 16h;
72%

Reference： [1]Waldhauser, Katri Maria; Toeroek, Michael; Ha, Huy-Riem; Thomet, Urs; Konrad, Daniel; Brecht, Karin; Follath, Ferenc; Kraehenbuehl, Stephan [Journal of Pharmacology and Experimental Therapeutics, 2006, vol. 319, # 3, p. 1413 - 1423]
[2]Ha; Stieger; Grassi; Altorfer; Follath [European Journal of Clinical Pharmacology, 2000, vol. 55, # 11-12, p. 807 - 814]

3
[ 52490-15-0 ]
[ 1951-26-4 ]

Yield	Reaction Conditions	Operation in experiment
98.8%	Stage #1: 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran With iodine; potassium carbonate In methanol; water at 40 - 65℃; Stage #2: With hydrogenchloride; sodium sulfite In methanol; water at 20 - 30℃; for 2h;	3.F F. Synthesis of Compounds of Formula 7 100.0 g (0.3397 mol) of the compound shown in Formula 6 and 215.6 g (0.8493 mol) of iodine elemental, 500 g of methanol,300g of water and 61.0g (0.4416mol) of potassium carbonate are mixed and reacted at 40-65°C for 8-10 hours.Add 30.0g (0.2378mol) of sodium sulfite aqueous solution to quench the reaction, and adjust the hydrochloric acid to the system pH of 1-2, 20-30°C,Incubate for 2 hours, and filter by suction to obtain a compound of the formula 7 and dry it at 70-75°C for 6 hours.Compound 183.2g was obtained as a light yellow solid powder with a yield of 98.8%.(Based on the compound represented by Formula 6), the GC purity was 99.6%.
72%	With iodine; sodium hydroxide In methanol at 0 - 20℃; for 3h;
	With iodine; iodic acid In acetic acid

0.914 g (47%)	With hydrogenchloride; sodium hydroxide; iodine In methanol	2.1 2-n-Butyl-3-(4-hydroxy-3,5-diiodobenzoyl)benzofuran Step 1 2-n-Butyl-3-(4-hydroxy-3,5-diiodobenzoyl)benzofuran At 0° C., to a stirred solution containing commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (1.05 g, 3.57 mmol) and sodium hydroxide (0.286 g, 7.14 mmol) in MeOH (35.7 mL) was added iodine (2.27 g, 8.93 mmol). After 24 h, the reaction was quenched with 1N HCl (30 mL) and extracted with ether. The combined ethereal extracts were washed with 10% aq. Na2 S2 O3 (3), with brine (3), dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil to give 0.914 g (47%) of the title compound. 1 H NMR (DMSO-d6) δ 0.85 (t, 3 H), 1.27 (sextet, 2 H), 1.71 (quintet, 2 H), 2.77 (t, 2 H), 7.29-7.36 (m, 2 H), 7.45 (d, 1 H), 7.65 (d, 1 H), 8.11 (s, 2 H), 10.5 (br s, 1 H).
14.61 g	With iodine; potassium carbonate In ethanol for 2h; Reflux;	1.4 4,Synthesis of 2-butyl-(4-hydroxy-3,5-diiodobenzoyl)benzofuran: Add to the 100 ml reaction bottle8 g of 2-butyl-(4-hydroxybenzoyl)benzofuran,15.18 grams of iodine,8.26 g of potassium carbonate and 48 ml of ethanol,The mixture was heated to reflux under stirring, and the reaction was kept for 2 hours, and the reaction was completed.Cool down to room temperature, filter, add the filtrate to the aqueous solution of sodium metabisulfite,After the completion of the dropwise addition, the mixture was stirred for 0.5 hour, filtered, and the filter cake was washed twice with water.The solid was dried under vacuum to give a white solid, 14.61 g.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN107382925, 2017, A Location in patent: Paragraph 0065-0067; 0095-0097; 0125-0127
[2]Huang, Wenbo; Xu, Jing; Liu, Changhui; Chen, Zhiyan; Gu, Yanlong [Journal of Organic Chemistry, 2019, vol. 84, # 5, p. 2941 - 2950]
[3]Ha; Stieger; Grassi; Altorfer; Follath [European Journal of Clinical Pharmacology, 2000, vol. 55, # 11-12, p. 807 - 814]
[4]Current Patent Assignee: PFIZER INC - US6103708, 2000, A
[5]Current Patent Assignee: ZHEJIANG POLY PHARMACEUTICAL; HAINAN POLY PHARMACEUTICAL - CN109988131, 2019, A Location in patent: Paragraph 0016

4
[ 1951-26-4 ]
[ 107-07-3 ]
(2-butylbenzofuran-3-yl)-[4-(2-hydroxyethoxy)-3,5-diiodophenyl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%
	In acetone at 50℃;

Reference： [1]Ha; Stieger; Grassi; Altorfer; Follath [European Journal of Clinical Pharmacology, 2000, vol. 55, # 11-12, p. 807 - 814]
[2]Waldhauser, Katri Maria; Toeroek, Michael; Ha, Huy-Riem; Thomet, Urs; Konrad, Daniel; Brecht, Karin; Follath, Ferenc; Kraehenbuehl, Stephan [Journal of Pharmacology and Experimental Therapeutics, 2006, vol. 319, # 3, p. 1413 - 1423]

5
[ 624-76-0 ]
[ 1951-26-4 ]
(2-butylbenzofuran-3-yl)-[4-(2-hydroxyethoxy)-3,5-diiodophenyl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In acetone

Reference： [1]Ha, Huy Riem; Bigler, Laurent; Wendt, Barbara; Maggiorini, Marco; Follath, Ferenc [European Journal of Pharmaceutical Sciences, 2005, vol. 24, # 4, p. 271 - 279]

6
[ 870-24-6 ]
[ 1951-26-4 ]
[4-(2-aminoethoxy)-3,5-diiodophenyl]-(2-butylbenzofuran-3-yl)methanone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With potassium carbonate In water; toluene

Reference： [1]Ha, Huy Riem; Bigler, Laurent; Wendt, Barbara; Maggiorini, Marco; Follath, Ferenc [European Journal of Pharmaceutical Sciences, 2005, vol. 24, # 4, p. 271 - 279]

7
[ 3647-69-6 ]
[ 1951-26-4 ]
2-n-butyl-3-(3,5-diiodo-4-β-N-morpholinoethoxybenzoyl)benzofuran hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In water; toluene

Reference： [1]Ha, Huy Riem; Bigler, Laurent; Wendt, Barbara; Maggiorini, Marco; Follath, Ferenc [European Journal of Pharmaceutical Sciences, 2005, vol. 24, # 4, p. 271 - 279]

8
[ 851025-42-8 ]
[ 1951-26-4 ]
[ 851025-45-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	With 18-crown-6 ether; potassium carbonate In acetone for 24h; Heating;

Reference： [1]Kalai, Tamas; Varbiro, Gabor; Bognar, Zita; Palfi, Anita; Hanto, Katalin; Bognar, Balazs; Osz, Erzsebet; Suemegi, Balazs; Hideg, Kalman [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 7, p. 2629 - 2636]

9
[ 4535-87-9 ]
[ 1951-26-4 ]
[ 96027-74-6 ]

Reference： [1]Journal of Pharmacology and Experimental Therapeutics,2006,vol. 319,p. 1413 - 1423

10
[ 107-99-3 ]
[ 1951-26-4 ]
(2-butylbenzofuran-3-yl)-[4-(2-dimethylaminoethoxy)-3,5-diiodophenyl]methanone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; toluene Heating;

11
[ 96-79-7 ]
[ 1951-26-4 ]
(2-butylbenzofuran-3-yl)-[4-(2-diisopropylaminoethoxy)-3,5-diiodophenyl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; toluene at 55 - 60℃;

Reference： [1]Bigler, Laurent; Spirli, Carlo; Fiorotto, Romina; Pettenazzo, Andrea; Duner, Elena; Baritussio, Aldo; Follath, Ferenc; Ha, Huy Riem [European Journal of Medicinal Chemistry, 2007, vol. 42, # 6, p. 861 - 867]

12
[ 5050-41-9 ]
[ 1951-26-4 ]
C₂₅H₂₇I₂NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; toluene at 55 - 60℃;

13
[ 1932-03-2 ]
[ 1951-26-4 ]
C₂₆H₂₉I₂NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; toluene at 55 - 60℃;

14
[ 109-54-6 ]
[ 1951-26-4 ]
C₂₄H₂₇I₂NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; toluene at 55 - 60℃;

15
[ 4584-46-7 ]
[ 1951-26-4 ]
(2-butyl-benzofuran-3-yl)-[4-(2-dimethylamino-ethoxy)-3,5-diiodo-phenyl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; toluene at 55 - 60℃;

16
[ 1951-26-4 ]
[4-(2-aminoethoxy)-3,5-diiodophenyl]-(2-butylbenzofuran-3-yl)methanone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / 1 h / Heating 2: 0.6 g / aq. HCl / 3.5 h / 130 °C

17
[ 1951-26-4 ]
2-n-butyl-3-(3,5-diiodo-4-carboxymethoxy-benzoyl)benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH / 16 h / 22 °C
	Multi-step reaction with 2 steps 1: K₂CO₃ / acetone / 24 h / 50 °C 2: 1 M aq. NaOH / methanol / 15 h / 50 °C

18
[ 1951-26-4 ]
2-n-butyl-3-(4-[(2-methoxyethoxy)methoxy]-3,5-diiodobenzoyl)benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.042 g (100%)	With sodium hydroxide; NaH In tetrahydrofuran; mineral oil	2.2 2-n-Butyl-3-(4-[(2-methoxyethoxy)methoxy]-3,5-diiodobenzoyl)benzofuran Step 2 2-n-Butyl-3-(4-[(2-methoxyethoxy)methoxy]-3,5-diiodobenzoyl)benzofuran At 0° C., to a stirred solution of 2-n-butyl-3-(4-hydroxy-3,5-diiodobenzoyl)benzofuran (0.897 g, 1.64 mmol) in THF (16.4 mL) was added 60% NaH/mineral oil (85.4 mg, 2.14 mmol). After 0.5 h, to the reaction was added MEM chloride (0.301 mL, 2.63 mmol) and the reaction was stirred for 18 h eventually warming to ambient temperature. The reaction was quenched with 1N NaOH (30 mL) and extracted with ether. The ethereal extracts were washed with 1N NaOH (3), with brine (3), dried (K2 CO3) and concentrated to give 1.042 g (100%) of the title compound. 1 H NMR (DMSO-d6) δ 0.85 (t, 3 H), 1.26 (sextet, 2 H), 1.70 (quintet, 2 H), 2.74 (t, 2 H), 3.28 (s, 3 H), 3.56 (t, 2 H), 4.03 (t, 2 H), 5.26 (s, 2 H), 7.28-7.40 (m, 2 H), 7.49 (d, 1 H), 7.66 (d, 1 H), 8.18 (s, 2 H).

Reference： [1]Current Patent Assignee: PFIZER INC - US6103708, 2000, A

19
[ 2969-81-5 ]
[ 1951-26-4 ]
2-butyl-3-[3,5-diiodo-4-(3-carboxypropyloxy)-benzoyl]benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium hydroxide; potassium carbonate In dichloromethane; water; isopropyl alcohol; acetonitrile	1 Example 1 Example 1 32.8 g (60 mmol) of 2-butyl-3-[3,5-diiodo-4-hydroxybenzoyl]benzofuran and 13.8 g (100 mmol) of anhydrous potassium carbonate are initially introduced into 200 ml of acetonitrile. 17.6 g (90 mmol) of ethyl 4-bromobutyrate are added dropwise at room temperature within the space of 30 minutes and the suspension is subsequently heated under reflux for 14 h. Once the reaction solution has been cooled down to room temperature, 200 ml of distilled water are added and the mixture is extracted 3 times with 100 ml of methyl tert-butyl ether. The combined organic extracts are dried and concentrated to dryness. The residue, which consists of 2-butyl-3-[3,5-diiodo-4-(3-ethoxycarbonyl-propyloxy)benzoyl]benzofuran, is introduced into 100 ml of isopropanol and a solution of 39.6 g (600 mmol) of 85% potassium hydroxide in 400 ml of distilled water is added. The suspension is heated at about 60° C. until a clear solution is formed. Once the solution has been cooled down to room temperature, 100 ml of 1N hydrochloric acid are added, and the mixture is adjusted to pH 3 with 32% hydrochloric acid while cooling, and then extracted 3 times with 200 ml of MTB ether on each occasion. The combined organic, dried, rotary-evaporated extracts are taken up in 50 ml of dichloromethane and left at 0° C. for several hours. The pale brown crystals which have precipitated out are stirred up with a further 50 ml of dichloromethane. After filtering with suction, washing and drying, 5.7 g (20%) of almost colourless crystals of 2-butyl-3-[3,5-diiodo-4-(3-carboxypropyloxy)-benzoyl]benzofuran are obtained which can, if desired, be further purified on a silica gel column (MTB ether/methanol=9:1).

Reference： [1]Current Patent Assignee: MERCK KGAA - US5399672, 1995, A

20
[ 5050-41-9 ]
[ 1951-26-4 ]
(2-butylbenzofuran-3-yl)-[3,5-diiodo-4-(2-pyrrolidine-1-yl-ethoxy)phenyl]-methanone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In water; toluene for 1h; Heating;

Reference： [1]Waldhauser; Brecht; Hebeisen; Ha; Konrad; Bur; Kraehenbuehl [British Journal of Pharmacology, 2008, vol. 155, # 4, p. 585 - 595]

21
[ 2008-75-5 ]
[ 1951-26-4 ]
(2-butylbenzofuran-3-yl)-[3,5-diiodo-4-(2-piperidin-1-yl-ethoxy)phenyl]-methanone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate In water; toluene for 1h; Heating;

Reference： [1]Waldhauser; Brecht; Hebeisen; Ha; Konrad; Bur; Kraehenbuehl [British Journal of Pharmacology, 2008, vol. 155, # 4, p. 585 - 595]

22
[ 60154-59-8 ]
[ 1951-26-4 ]
[ 1096359-59-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium iodide In N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Snead, Aaron N.; Miyakawa, Motonori; Tan, Edwin S.; Scanlan, Thomas S. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 22, p. 5920 - 5922]

23
[ 52490-15-0 ]
2-n-butyl-3-(3-iodo-4-hydroxybenzoyl)-benzofuran [ No CAS ]
[ 1951-26-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 25% 2: 11%	With potassium hydroxide; sodium hypochlorite; sodium iodide In methanol at -5℃; for 4h;

Reference： [1]Snead, Aaron N.; Miyakawa, Motonori; Tan, Edwin S.; Scanlan, Thomas S. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 22, p. 5920 - 5922]

24
[ 106-93-4 ]
[ 1951-26-4 ]
[ 96027-84-8 ]

Yield	Reaction Conditions	Operation in experiment
61%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;
	Stage #1: 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran With potassium carbonate In butanone for 0.5h; Reflux; Stage #2: ethylene dibromide In butanone for 8h; Reflux;	1 General procedure: The 2-butylbenzofuran-3-yl (4-hydroxy-3,5-diiodophenyl)methanone (10 mmol) was dissolved in 50 ml of methyl ethyl ketone.Then, potassium carbonate (20 mmol) was slowly added thereto and heated under reflux for 0.5 h, and then dibromoethane or dibromopropane (20 mmol) was slowly added dropwise.After refluxing for 8 hours, the potassium carbonate solid was removed by suction filtration, washed with methyl ketone, and the filtrate was collected and the solvent was evaporated.Subsequently, it was extracted with chloroform (3 x 30 ml).The crude product was purified by silica gel column chromatography, petroleum ether:Ethyl acetate (50:1) was used as the mobile phase to afford intermediates as white solid.

Reference： [1]Snead, Aaron N.; Miyakawa, Motonori; Tan, Edwin S.; Scanlan, Thomas S. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 22, p. 5920 - 5922]
[2]Current Patent Assignee: SICHUAN UNIVERSITY - CN108218814, 2018, A Location in patent: Paragraph 0030; 0031; 0032

25
[ 1951-26-4 ]
[ 1469440-79-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine; dmap / 0.67 h / 23 °C 2: copper(l) iodide / N,N-dimethyl-formamide / 0.67 h / 80 °C / Inert atmosphere 3: potassium carbonate; methanol / 1 h / 23 °C 4: potassium carbonate; sodium iodide / toluene; water / 0.75 h / 100 °C