2-(2-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone (JWH-250) [C22H25NO2]

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5 reactions in Reaxys

2018-03-04 20h:42m:43s (EST)

N

1. Query

O

O

Search as: As drawn

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N

O O Cl

O

O

Rx-ID: 37147375 View in Reaxys 1/5 Yield

Conditions & References Reaction Steps: 2 1: thiophen-2-yl magnesium bromide; ammonium chloride / diethyl ether 2: mineral oil; water; dichloromethane With ammonium chloride, thiophen-2-yl magnesium bromide in diethyl ether, dichloromethane, water, mineral oil Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698384; (2014); (A1) English View in Reaxys

N

NH

O

O

Rx-ID: 37147380 View in Reaxys 2/5 Yield

Conditions & References Reaction Steps: 2 1: thiophen-2-yl magnesium bromide; ammonium chloride / diethyl ether 2: mineral oil; water; dichloromethane With ammonium chloride, thiophen-2-yl magnesium bromide in diethyl ether, dichloromethane, water, mineral oil Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698384; (2014); (A1) English View in Reaxys

O O

Br

O

O

N

N

NH O

O

O

Rx-ID: 37147388 View in Reaxys 3/5 Yield 41 %

Conditions & References 3 : Example 3 Example 3 Preparation of 2-(2-methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (JWH-250) 4 60percent Sodium hydride in mineral oil (1.8g, 45.23mmol) was suspended in dimethylformamide (100ml) and 1(1H-indol-3-yl)-2-(2-methoxyphenyl)ethanone 3 (10g, 37.70mmol) was added portionwise at room temperature, allowing to stir further 45 min at room temperature after the addition was finished. 1-Bromopentane (7.02ml, 56.55mmol) was added dropwise at room temperature and the reaction mixture was stirred at room temperature overnight.

Water (200ml) was added and the mixture was extracted three times with ethyl acetate (3x200ml).

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The organic fractions were combined, washed with water (200ml) and brine (200ml) and dried over sodium sulphate and concentrated in vacuo.

The residue was purified by column chromatography (Biotage Isolera 4, SNAP-100g, 5percent-20percent ethyl acetate hexane containing 5percent dichloromethane) to give 6.2g (41percent ) of 2-(2-methoxyphenyl)-1-(1-pentyl-1Hindol-3-yl)ethanone (JWH-250) 4 as an orange/tan solid. in dichloromethane, water, mineral oil Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698384; (2014); (A1) English View in Reaxys

O

N

HO O O

O

Rx-ID: 37147402 View in Reaxys 4/5 Yield

Conditions & References Reaction Steps: 3 1: thionyl chloride 2: thiophen-2-yl magnesium bromide; ammonium chloride / diethyl ether 3: mineral oil; water; dichloromethane With ammonium chloride, thiophen-2-yl magnesium bromide in thionyl chloride, diethyl ether, dichloromethane, water, mineral oil Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698384; (2014); (A1) English View in Reaxys

O

N

Cl N

O O

O

Rx-ID: 9986543 View in Reaxys 5/5 Yield

Conditions & References Stage 1: With dimethylaluminum chloride in dichloromethane, T= 0 °C Stage 2: in dichloromethane, T= 0 °C Huffman, John W.; Szklennik, Paul V.; Almond, Amanda; Bushell, Kristen; Selley, Dana E.; He, Hengjun; Cassidy, Michael P.; Wiley, Jenny L.; Martin, Billy R.; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 18; (2005); p. 4110 - 4113 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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