942589-44-8|Methyl 5-iodo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate| Ambeed

Yield	Reaction Conditions	Operation in experiment
		To a solution of lithium diisopropylamide (26 mL, 2M solution in heptane/tetrahydrofuran) in THF (80 mL) at -780C under nitrogen was added drop wise a solution of Intermediate 1 (4 g) in THF (60 mL). The reaction was stirred for 10 min and iodine (12 g) in THF (60 mL) was added slowly to the reaction. Stirring was continued at -780C under nitrogen for a further 1.5 h. The reaction was neutralised with ammonium chloride and washed with 5% sodium thiosulphate solution. The organics were washed with brine, dried (Na2SO4) and concentrated to give an oil. The crude product was then purified by Biotage silica chromatography eluting with EtOAc in cyclohexane (2.5%) to give the title compound. MS calcd for (C8H5F3INO3S - H)": 378 MS found (electrospray): (M-H)"= 378
		Intermediate 7 Methyl 5-iodo-3-[(trifluoroacetyl)amino]-2-thiophenecarboxylateTo a solution of LDA (2M in THF, 26 ml.) was added THF (80 ml.) at -78 0C under nitrogen, followed by a solution of <strong>[79128-68-0]methyl 3-[(trifluoroacetyl)amino]-2-thiophenecarboxylate</strong> (Intermediate 1 ) (4 g, 2.59 mmol) in THF (60 ml.) via syringe over 30 mins. After complete addition, the mixture was left for 15 mins, then iodine (4g, 15.8 mmol) in THF (40 ml.) was added via syringe over 30 mins at -780C. The mixture was quenched by the addition of ammonium chloride, then ethyl acetate added at room temperature. The organic fraction was separated, washed with sodium thiosulphate solution (50%) and brine, the organic layer was dried (Na2SO4) and evaporated. The crude material was purified by ISCO Companion silica chromatography, eluting with a gradient 0-20% ethyl acetate in cyclohexane to give the title compound. Further quantities were obtained by collecting the early eluting fractions and further purification by ISCO Companion silica chromatography, eluting with a gradient 0-10% ethyl acetate in cyclohexane to give the title compound. MS calcd for (C8H5F3INO2S - H)" : 378 MS found (electrospray): (M+H)" = 378

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol; water; at 20℃; for 1h;	Potassium carbonate (8.1 g) was added in one portion to Intermediate 2 (3.7 g) in MeOH (130 mL) and water (18.5 mL) at room temperature. The reaction was stirred for 1 h, then partitioned between water and EtOAc. The organics were washed with brine, dried (Na2SO4 ) and concentrated to give the title compound. MS calcd for (C6H6INO2S + H)+: 284 MS found (electrospray): (M+H)+ = 284
	With potassium carbonate; In methanol; water; at 20℃; for 18h;	Intermediate 8 Methyl S-amino-delta-iodo^-thiophenecarboxylate <n="34"/>A mixture of methyl 5-iodo-3-[(trifluoroacetyl)amino]-2-thiophenecarboxylate (Intermediate 7) (0.98 g, 2.59 mmol) and potassium carbonate (1.8 g, 13 mmol) in methanol (60 ml.) and water (6 ml.) was stirred at room temperature for 18 h. The solvent was evaporated and partitioned between water (30 ml.) and DCM (50 ml_), then passed through a hydrophobic frit and the organic fraction evaporated. The crude material was purified by ISCO Companion silica chromatography, eluting with a gradient of 0-20% ethyl acetate in cyclohexane to give the title compound. Further quantities were obtained by collecting the early eluting fractions and further purification by ISCO Companion silica chromatography, eluting with a gradient 0-50% DCM in cyclohexane.MS calcd for (C6H6INO2S + H)+: 284MS found (electrospray): (M+H)+ = 284

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Methyl 5-iodo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

CAS No.: 942589-44-8

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Product Details of [ 942589-44-8 ]

Safety of [ 942589-44-8 ]

Application In Synthesis of [ 942589-44-8 ]

[ 942589-44-8 ] Synthesis Path-Downstream 1~2

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
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H301	Toxic if swallowed
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H303	May be harmful if swallowed