[ CAS No. 19658-77-6 ] {[proInfo.proName]}

Name: 19658-77-6|1-Iodoisoquinoline|98%
Brand: Ambeed
SKU: A962859
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Quality Control of [ 19658-77-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 19658-77-6 ]

Product Details of [ 19658-77-6 ]

CAS No. :	19658-77-6	MDL No. :	MFCD00234494
Formula :	C₉H₆IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FDDBUIWRNBGXHB-UHFFFAOYSA-N
M.W :	255.06	Pubchem ID :	640964
Synonyms :

Safety of [ 19658-77-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	1759
Hazard Statements:	H302-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 19658-77-6 ]

* 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 [ 19658-77-6 ]
Downstream synthetic route of [ 19658-77-6 ]

[ 19658-77-6 ] Synthesis Path-Upstream 1~1

1
[ 19658-77-6 ]
[ 86520-96-9 ]

Reference： [1] Synthesis, 1983, # 4, p. 312 - 314

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Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 1-chloroisoquinoline With sodium iodide In propiononitrile at 20℃; Inert atmosphere; Stage #2: With chloro-trimethyl-silane In propiononitrile for 15h; Reflux;
81%	With chloro-trimethyl-silane; sodium iodide In various solvent(s) for 24h; Heating;
59%	Stage #1: 1-chloroisoquinoline With para-fluorostyrene; C₁₈H₂₁OZn^(1-)Cl^(1-)Mg⁽²⁺⁾; cobalt acetylacetonate In tetrahydrofuran at 50℃; for 4h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: isoquinoline With N-tetramethylpiperidine magnesium chloride; lithium chloride In tetrahydrofuran at 25℃; for 2h; Stage #2: With iodine In tetrahydrofuran at -20℃;
92%	Stage #1: isoquinoline With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere;
90%	Stage #1: isoquinoline With C₉H₁₇NPol^(1-)Cl^(1-)Mg⁽²⁺⁾*ClLi at 20℃; for 2h; Stage #2: With iodine

81%	Stage #1: isoquinoline With (2,2,6,6-tetramethylpiperidido)<SUB>2</SUB>Ag(CN)Li<SUB>2</SUB><SUB> </SUB> In tetrahydrofuran at 0℃; for 2h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 3h; chemoselective reaction;
76%	Stage #1: isoquinoline With TMPMgCl*LiCl In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; regioselective reaction;
	With 2,2,6,6-tetramethylpiperidinyl-lithium; iodine; di-tert-butylzinc 1.) THF, RT, 2.) THF, RT; Yield given; Multistep reaction;
	Stage #1: isoquinoline at 20℃; for 2h; Stage #2: With iodine	Chimassorb 994 can be used to prepare the corresponding mixed Mg/Li amide by reacting chimassorb 994 with i-PrMgCl·LiCl at room temperature (see Scheme 5). This base is stable and soluble in THF before and after deprotonation. As being a polymeric base, it can be easily removed after completion of the reaction. Since chimassorb 994 is much cheaper than TMP, a corresponding base can be prepared at reduced costs. The polymeric base 34 shows slightly lower activity than monomeric TMPMgCl·LiCl but is nevertheless very effective in deprotonating compounds with acidic protons like isoquinoline. A corresponding example is shown in Scheme 7. The polymeric base can be used to deprotonate various substrates. For example, isoquinoline reacts at room temperature with the base 34 affording after quenching with iodine 1-iodoisoquinoline 7a.

Yield	Reaction Conditions	Operation in experiment
96%	With iodine In tetrahydrofuran at -20℃;	A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with TMPMgCl-LiCl (5 mL, 1.2 M in THF, 6.0 mmol). Isoquinoline (703 mg, 5.45 mmol) in THF (5 ml) was added dropwise at room temperature. During addition, the reaction mixture became red and the metal ation was complete after 2 h (as checked by GC analysis of reaction aliquots quenched with a solution of I2 in THF, the conversion was more than 98%). A solution of I2 in THF (6 ml, 1 M in THF, 6.0 mmol) was slowly added at -200C. The reaction mixture was quenched with sat. aqueous NH4Cl solution (10 mL). The aqueous phase was extracted with ether (4 x 10 mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by filter column chromatography (GE^CVpentane) yielding 1-iodoisoquinoline (7a; 1.33 mg, 96%) as slightly yellow crystals (mp = 74-76°C).
	With iodine In tetrahydrofuran at -20℃;	1 Preparation of 1-iodoisoquinoline (7a): ; A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with TMPMgCl·LiCl (5 mL, 1.2 M in THF, 6.0 mmol). Isoquinoline (703 mg, 5.45 mmol) in THF (5 ml) was added dropwise at room temperature. During addition, the reaction mixture became red and the metalation was complete after 2 h (as checked by GC analysis of reaction aliquots quenched with a solution of I2 in THF, the conversion was more than 98%). A solution of I2 in THF (6 ml, 1 M in THF, 6.0 mmol) was slowly added at -20°C. The reaction mixture was quenched with sat. aqueous NH4Cl solution (10 mL). The aqueous phase was extracted with ether (4 x 10 mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by filter column chromatography (CH2Cl2/pentane) yielding 1-iodoisoquinoline (7a; 1.33 mg, 96%) as slightly yellow crystals (mp = 74-76°C). The products listed in table 1 below can be produced according to the preparation of 1-iodoisoquinoline (7a). The activity of the amides (I) can be shown on the basis of the magnesiation of isoquinoline. Diisopropylamido magnesium chloride-lithium chloride 5a leads to the magnesiated isoquinoline 6 after 12 h reaction time at 25°C and by using 2 equivalents of the base. After iodolysis, the iodoisoquinoline 7a is isolated in 88% yield (Scheme 2). Even more active is the sterically more hindered and less aggregated 2,2,6,6-tetramethylpiperidino magnesium chloride-lithium chloride reagent 5b. It leads to a complete magnesiation within 2 h at 25°C. Remarkably, with this base only 1.1 equivalents are required to achieve a complete metalation. The resulting Grignard reagent 6 provides after iodolysis, the iodoisoquinoline 7a in 96% yield (Scheme 2 and Table 1).

[ CAS No. 19658-77-6 ] {[proInfo.proName]}

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[ 19658-77-6 ] Synthesis Path-Upstream 1~1

[ 19658-77-6 ] Synthesis Path-Downstream 1~88

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	With trimethylstannylsodium; iodine 1.) DME, 3 h, cooling 2.) CHCl₃, 15 min, room temp.; Yield given. Multistep reaction;
	With chloro-trimethyl-silane; sodium iodide In acetonitrile for 15h; Reflux; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
83%	With palladium diacetate; potassium carbonate; triphenylphosphine In monoethylene glycol diethyl ether for 18h; Reflux; Inert atmosphere;
70%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water for 6h; Reflux; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 1-iodoisoquiniline With TurboGrignard In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: With N-fluorobis(benzenesulfon)imide In dichloromethane; octadecafluorodecahydronaphthalene (cis+trans) at -78 - 25℃; Inert atmosphere;
79 %Spectr.	With tetramethylammonium fluoride In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Sealed tube;

Yield	Reaction Conditions	Operation in experiment
65%	With di-μ-iodobis(tri-t-butylphosphino)dipalladium(l) In toluene at 80℃;
55%	With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; 4,4'-Dimethoxy-2,2'-bipyridin In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;

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