[ CAS No. 73220-42-5 ]

Name: 73220-42-5|3-Iodo-7-methoxy-4H-chromen-4-one|95%
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Quality Control of [ 73220-42-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 73220-42-5 ]

Product Details of [ 73220-42-5 ]

CAS No. :	73220-42-5	MDL No. :	MFCD02168928
Formula :	C₁₀H₇IO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RAMRIHLZEAHUBU-UHFFFAOYSA-N
M.W :	302.07	Pubchem ID :	848817
Synonyms :

Safety of [ 73220-42-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 73220-42-5 ]

* 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 [ 73220-42-5 ]
Downstream synthetic route of [ 73220-42-5 ]

[ 73220-42-5 ] Synthesis Path-Upstream 1~1

1
[ 292638-85-8 ]
[ 73220-42-5 ]
[ 42059-83-6 ]
[ 5751-52-0 ]

Yield	Reaction Conditions	Operation in experiment
70.5%	With copper diacetate; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 6 h; Inert atmosphere; Green chemistry	To a solution of 3-iodo-7-methoxy-4H-chromen-4-one (1) (4 mmol) and methyl acrylate (2) (4.8 mmol) in solvent was added catalyst (5 mmol percent) and base (8 mmol). The reaction mixture was stirred via oil heating under nitrogen protection. Then the mixture was poured into 10percent HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compound 3 or 4.

Reference： [1] Tetrahedron, 2012, vol. 68, # 47, p. 9777 - 9787

[ 73220-42-5 ] Synthesis Path-Downstream 1~12

1
[ 5720-07-0 ]
[ 73220-42-5 ]
[ 1157-39-7 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 4408 - 4410
[2]Organic Letters,2017,vol. 19,p. 2981 - 2984
[3]ChemMedChem,2013,vol. 8,p. 633 - 643

2
[ 5751-52-0 ]
[ 73220-42-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7106 - 7109
[2]Tetrahedron,2012,vol. 68,p. 9777 - 9787
[3]European Journal of Medicinal Chemistry,2013,vol. 62,p. 158 - 167

3
[ 29427-58-5 ]
[ 536-74-3 ]
[ 73220-42-5 ]
[ 1248338-82-0 ]

Reference： [1]Journal of Combinatorial Chemistry,2010,vol. 12,p. 895 - 899

4
[ 292638-85-8 ]
[ 73220-42-5 ]
[ 42059-83-6 ]
[ 5751-52-0 ]

Yield	Reaction Conditions	Operation in experiment
70.5%; 5%	With copper diacetate; palladium diacetate; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 100℃; for 6h;Inert atmosphere; Green chemistry;	To a solution of 3-iodo-7-methoxy-4H-chromen-4-one (1) (4 mmol) and methyl acrylate (2) (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via oil heating under nitrogen protection. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compound 3 or 4.

Reference： [1]Tetrahedron,2012,vol. 68,p. 9777 - 9787

5
[ 2210-24-4 ]
[ 73220-42-5 ]
[ 1412410-76-4 ]

Yield	Reaction Conditions	Operation in experiment
94.2%	With triethylamine at 80℃; for 2h;	3.2. general experimental for ILPd-MNPs catalyzed heck cross coupling reaction and catalyst recycling General procedure: The solution of 3-iodo-7-methoxy-4H-chromen-4-one (1)(1 mmol), methy acrylate (2) (1.2mmol) was allowed to reactin presence of freshly prepared ILPd MNP (0.1 g) with 0.250 mmol of the base as per the reaction condition defined in Table 2. After cooling the reaction mass the volatile materials were under reduced pressure at 40oC for 20 minutes.Then the reaction product was isolated with diethyl ether(5x2mL) washing. Then the purification of the reaction product was carried out with flash chromatography (eluent:AcOEt: n-hexane=1: 3) to achieve the pure Heck reaction product.
79%	With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; for 0.116667h; Microwave irradiation;	6.3 General procedure for the synthesis of compounds 7 and 8 General procedure: To a solution of compound 5 (6) (3 mmol) and substituted acrylamide (3.3 mmol) in dry DMF was added Pd(OAc)2 (3%) and triethylamine (6 mmol). The reaction mixture was stirred under 100 °C via microwave (500 w) for 7 min. Then the mixture was poured into 10% HCl ice water (200 ml) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compounds 7 or 8.
	With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 80℃; for 0.0833333h; Microwave irradiation; Green chemistry;	4.3. General experimental procedure for Heck reaction under microwave heating condition General procedure: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.

Reference： [1]Gautam, Prashant; Srivastava, Vivek [Letters in Organic Chemistry, 2021, vol. 18, # 5, p. 359 - 372]
[2]Zhang, Yikai; Zhong, Hanyu; Lv, Zhiliang; Zhang, Mingfeng; Zhang, Tao; Li, Qisheng; Li, Ke [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 158 - 167]
[3]Zhang, Yikai; Lv, Zhiliang; Zhong, Hanyu; Zhang, Mingfeng; Zhang, Tao; Zhang, Wannian; Li, Ke [Tetrahedron, 2012, vol. 68, # 47, p. 9777 - 9787]

6
[ 13304-62-6 ]
[ 73220-42-5 ]
[ 1412410-79-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 100℃; for 0.116667h;Microwave irradiation;	General procedure: To a solution of compound 5 (6) (3 mmol) and substituted acrylamide (3.3 mmol) in dry DMF was added Pd(OAc)2 (3%) and triethylamine (6 mmol). The reaction mixture was stirred under 100 C via microwave (500 w) for 7 min. Then the mixture was poured into 10% HCl ice water (200 ml) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compounds 7 or 8.
	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 0.0833333h;Microwave irradiation; Green chemistry;	General procedure: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 62,p. 158 - 167
[2]Tetrahedron,2012,vol. 68,p. 9777 - 9787

7
[ 5453-48-5 ]
[ 73220-42-5 ]
C₁₉H₁₄ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 100℃; for 0.116667h;Microwave irradiation;	General procedure: To a solution of compound 5 (6) (3 mmol) and substituted acrylamide (3.3 mmol) in dry DMF was added Pd(OAc)2 (3%) and triethylamine (6 mmol). The reaction mixture was stirred under 100 C via microwave (500 w) for 7 min. Then the mixture was poured into 10% HCl ice water (200 ml) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compounds 7 or 8.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 62,p. 158 - 167

8
[ 57508-48-2 ]
[ 73220-42-5 ]
ethyl 2-amino-5-(2-hydroxy-4-methoxybenzoyl)-1H-pyrrole-3-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4186 - 4189

9
[ 663954-31-2 ]
[ 73220-42-5 ]
[ 2267264-87-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 80℃; for 4.5h; Inert atmosphere;

Reference： [1]Wang, Pei; Zhang, Jin; Wang, Tao; Liang, Yong; Zhang, Zunting [Organic and Biomolecular Chemistry, 2019, vol. 17, # 4, p. 851 - 858]

10
[ 1061350-97-7 ]
[ 73220-42-5 ]
[ 2267264-97-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 80℃; for 4.5h; Inert atmosphere;

Reference： [1]Wang, Pei; Zhang, Jin; Wang, Tao; Liang, Yong; Zhang, Zunting [Organic and Biomolecular Chemistry, 2019, vol. 17, # 4, p. 851 - 858]

11
[ 3189-13-7 ]
[ 73220-42-5 ]
6-methoxy-2-[(6-methoxy-1H-indol-1-yl)methylene]-3(2H)-benzofuranone [ No CAS ]
7-methoxy-2-(6-methoxy-1H-indol-1-yl)-4H-1-benzopyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 36% 2: 16%	With potassium carbonate In N,N-dimethyl-formamide at 80℃;	General procedure for preparation of 2-(1H-indol-1-ylmethylene)-3(2H)-benzofuranone and 2-(1H-indol-1-yl)-4H-1-benzopyran-4-one derivatives (1-13) General procedure: The title compounds were synthesized according to a previous method [20]. A mixture of 3-iodochromone (2 mmol), the appropriate indole (4 mmol) and K2CO3 (20 mmol) in DMF (20 mL) was stirred at 80 °C for 2-6 h. The reaction mixture was extracted with water and CHCl3. The organic layer was dried over Na2SO4 and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:AcOEt=20:1) to give the 2-(1H-indol-1-ylmethylene)-3(2H)-benzofuranone derivatives (1a-13a) and the 2-(1H-indol-1-yl)-4H-1-benzopyran-4-one derivatives (1b-11b).

Reference： [1]Takao, Koichi; U, Shiori; Kamauchi, Hitoshi; Sugita, Yoshiaki [Bioorganic Chemistry, 2019, vol. 87, p. 594 - 600]

12
[ 2251-76-5 ]
[ 73220-42-5 ]
3-(4-fluorobenzoyl)-7-methoxy-4H-chromen-4-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 7152 - 7174

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[ CAS No. 73220-42-5 ]

Quality Control of [ 73220-42-5 ]

Related Doc. of [ 73220-42-5 ]

Product Details of [ 73220-42-5 ]

Safety of [ 73220-42-5 ]

Application In Synthesis of [ 73220-42-5 ]

[ 73220-42-5 ] Synthesis Path-Upstream 1~1

[ 73220-42-5 ] Synthesis Path-Downstream 1~12

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