898566-17-1

898566-17-1 - Names and Identifiers

Name	2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene
Synonyms	Canagliflozin INT5 2-(4-Fluorophenyl) Canagliflozin iMpurity D Canagliflozin Intermediate1 2-(4-Fluorophenyl)-5-(5-iodo-2-Methylbenzyl)thiophene 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene 2-((5-IODO-2-METHYLPHENYL)METHYL)-5-(4-FLUOROPHENYL)THIOPHENE 2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]-Thiophene Thiophene, 2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]-
CAS	898566-17-1
EINECS	618-312-6
InChI	InChI=1/C18H14FIS/c1-12-2-7-16(20)10-14(12)11-17-8-9-18(21-17)13-3-5-15(19)6-4-13/h2-10H,11H2,1H3

898566-17-1 - Physico-chemical Properties

Molecular Formula	C18H14FIS
Molar Mass	408.27
Density	1.533
Melting Point	109-110 °C
Boling Point	450.2±45.0 °C(Predicted)
Solubility	DMSO (Sparingly), Methanol (Slightly)
Vapor Presure	0-0Pa at 20-25℃
Appearance	Solid
Color	Pale Yellow
Storage Condition	2-8°C(protect from light)
Refractive Index	1.643

898566-17-1 - Reference Information

LogP	7.5 at pH7
Use	2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl) methyl] thiophene is an antidiabetic and canagliflozin intermediate. Canagliflozin is an inhibitor of sodium/glucose cotransporter 2(SGLT2) and is a drug candidate for the treatment of type 2 diabetes and obesity.
Application	2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl) methyl] thiophene can be used as a pharmaceutical intermediate for the synthesis of other compounds with certain activity, such as the preparation of compounds with anti sodium dependent glucose transporter (SGLT) inhibitory activity.
preparation	Step 1: 4-fluoro-phenylmagnesium bromide to Mg(19.44g,0.8mol) 2-Me-THF(80ml,0.1L / mole) was added and stirred slowly. Dissolve 1-bromo-4-fluoro-benzene (142.8g,0.816mole) in 2-Me-THF (0.25 ml, L / mole), 25ml of this solution was added to the Mg mixture. The resulting mixture was heated to about 43 °c and the remainder of the 1-bromo-4-fluorobenzene solution was added over about 40 minutes while maintaining the mixture at reflux temperature. The addition funnel to which 1-bromo-4-fluorobenzene was added was rinsed with 2-methyl-thf (40ml), and the washing solution was added to the reaction solution. The resulting mixture was stirred at 90 °c for 1 hour and cooled to 20 °c to give a brown-green solution containing 4-fluoro-phenylmagnesium bromide. Step 2:2-(4-fluorophenyl) thiophene 2-bromothiophene (130.4g,0.8mol) was dissolved in 2-Me-THF(240ml,0.3L/mole), and the resulting mixture was cooled to 2 °c, and NiCl 2(dppe)(2.11g,4.0mmol) was added at ≤ 30 °c, the 4-fluoro-phenylmagnesium bromide solution prepared in Step A was added to give A dark red solution. The solution was then stirred at 22 °c for 1.5 H, a solution of acetic acid (91.7ml,1.6mol) in water (240ml,0.3L / mol) was added, the resulting mixture was stirred vigorously for 15 minutes, the layers were separated, the organic layer was washed with water (80ml,0.1L/ mol), concentrated in vacuo at 75 °c, 2-(4-fluorophenyl) thiophene is obtained as a brown oil. Step 3:2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl) methyl] THIOPHENE DCM (91.7 ml,1L / mol) was added to 91.7g of 5-iodo-2-methylbenzoic acid (0.35g, mol) and stirred at 22 °c, thionyl chloride (42.5g,0.35mol) was added to the resulting mixture using an addition funnel, and the resulting mixture was slowly heated to reflux temperature (at which point the mixture became a colorless solution and gas evolution was observed), stir for 1 hour and cool to 2 °c. Aluminum chloride particles (56.0g,0.42mol) were respectively added to the resulting mixture, stirred at 2 °c for 15 minutes, and then dissolved in DCM(0.5L / mol) was added with an addition funnel 2-(4-fluorophenyl) thiophene (0.35mol,89.7% w / w), and the temperature was increased to 20 °c. The resulting mixture was stirred at 20 °c for 2 hours, then cooled to 2 °c, the remaining aluminum chloride particles (107.3g,0.805mol ) were added, and the resulting mixture was stirred for 15 minutes. Acetonitrile (210ml,0.6L / mol) was added with a dropping funnel at T ≤ 20 °c over 20 minutes, and tetramethyldisiloxane (131.6g,0.98mol), after which the resulting mixture was slowly heated to reflux temperature (42 °c), maintained at reflux for 3 hours, allowed to cool to 22 °c, and then stirred for 16 hours. Water (420ml,1.2L / mol) was added within 30 min at T ≤ 35 °c, and the resulting mixture was stirred vigorously for 15 min, 0.2L / mol) the organic layer was washed and then concentrated in vacuo at 50 °c to give 2-(4-fluorophenyl)-Crude 5-[(5-iodo-2-methylphenyl) methyl] thiophene. Dissolve crude 2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl) methyl] thiophene (62.0g,0.1mol) in ethyl acetate (40ml) to a mixture of 2-propanol (50ml), activated carbon (1.2g) was added to the resulting mixture, and the resulting mixture was heated to reflux, and then stirred under reflux for 15 minutes. The resulting mixture was filtered with filter aid, the filter was washed with ethyl acetate (10ml), and the combined filtrate and washings were cooled to 2 °c over 16 hours and crystallized spontaneously. The precipitate was filtered and washed with 2-propanol (50ml), dried under vacuum at 60 °c to give solid 2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl) methyl] thiophene.

Last Update：2024-04-10 22:29:15

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View History

898566-17-1

898566-17-1

2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene

CAS: 898566-17-1

Molecular Formula: C18H14FIS

898566-17-1 - Names and Identifiers

898566-17-1 - Physico-chemical Properties

898566-17-1 - Reference Information

Supplier List

898566-17-1 Request for Quotation

2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene

CAS: 898566-17-1

Molecular Formula: C18H14FIS

898566-17-1 - Names and Identifiers

898566-17-1 - Physico-chemical Properties

898566-17-1 - Reference Information

Supplier List

898566-17-1