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SGT-263 (CUMYL-5F-P7AICA)

William D.

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Reaction scheme:
0x58bGwhPS

Synthesis:
1. A solution of 1H-pyrrolo[2, 3-b]pyridine-3-carboxylic acid (0.49 g, 3 mmol), oxalyl chloride (0.6 mL, 7.2 mmol), and DMF (1 mL) in dichloromethane (20 mL) was stirred for 20 min.
2. The mixture was evaporated and then redissolved in methanol (20 mL) and stirred for 40 min.
3. The mixture was evaporated and then extracted with ethyl acetate.
4. The organic phase was washed with saturated sodium bicarbonate solution and dried with Na2SO4, and the solvent was removed in vacuo to yield the white solid (0.36 g, 68%).
5. A solution of Step 4 (0.36 g, 2 mmol), potassium t-butoxide (0.27 g, 2.4 mmol), and 1-bromo-5-fluoropentane (1.6 g,9.5 mmol) in THF (20 mL) was stirred for 24 h.
6. The mixture was extracted with ethyl acetate.
7. The organic phase was washed with brine and dried with Na2SO4, and the solvent was removed in vacuo.
8. The residue was purified by silica gel chromatography with stepwise gradient elution of n-hexane/ethyl acetate (3:1–2:1–1:1, v/v) to yield the white solid (0.35 g, 65%).
9. A solution of step 8 (0.35 g, 1.3 mmol) and 6 mol/L sodium hydroxide solution (10 mL) in methanol/THF (2:1,v/v, 15 mL) was stirred for 1.5 days.
10. The mixture was evaporated, added to water, and then washed with ethyl acetate.
11. A solution of 1 mol/L hydrochloric acid was added to the aqueous phase, and the mixture was extracted with ethyl acetate.
12. The organic phase was washed with brine and dried with Na2SO4, and the solvent was removed in vacuo to yield the white solid (0.39 g, quant.)
13. A solution of step 12 (0.39 g, 1.3 mmol), oxalyl chloride (3 mmol), and DMF (1 mL) in dichloromethane (12 mL) was stirred for 10 min.
14. The mixture was evaporated and then redissolved in dichloromethane (10 mL).
15. Cumylamine (2 mmol) and triethylamine (0.5 mL) were added to the solution and stirred for 15 h.
16. The mixture was evaporated and then extracted with ethyl acetate.
17. The organic phase was washed with 0.1 mol/L hydrochloric acid solution, saturated sodium bicarbonate solution and brine, and then dried with Na2SO4, and the solvent was removed in vacuo to yield the white solid (0.37 g, 77%).
 
Last edited by a moderator:

onionexpress

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Thank you very much ! Can you give me proportions for 1kg end product ?
 

MuricanSpirit

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Thank you very much ! Can you give me proportions for 1kg end product ?
onionexpressJust multiply everything with 370x (1000g/0.37g = 370 ratio) as "ground rule".

Of course I'm sure some solvents allow higher density mixture eg. you wont need 370x more ethyl acetate but you quickly notice when the solution is over saturated but keep in mind more heat allows more saturation (not sure why).
 

onionexpress

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Just multiply everything with 370x (1000g/0.37g = 370 ratio) as "ground rule".

Of course I'm sure some solvents allow higher density mixture eg. you wont need 370x more ethyl acetate but you quickly notice when the solution is over saturated but keep in mind more heat allows more saturation (not sure why).
ArsoleDickiteThanks for that I appreciate it. But im newbie and I need specific informations to avoid mistakes.
 

onionexpress

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Can anyone upload a tutorial video? I’m newbie and i won’t to know every step (including equipment needed). I would be thankful thanks a lots
 

BackstagePanther

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Hello, is this analogue to the 5F-CUMYL-PEGACLONE (5F-SGT-151) ?
Do you intend to upload a synthesis of it as well? It would be more than interesting.
Thank you for your tremendous work.
 

BackstagePanther

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Oh, I just realized, the base of 5F-SGT-151 contains and a whole 3rd benzene ring. Uploading nomenclature.
Was wondering if the 5F-SGT-151 could be crafted and instead of 1-bromo-5-fluoropentane used as tail,
we could use 1-bromo-6-fluorohexane. Would this give us even bigger receptor affinity / effects?
 

Attachments

  • sVTSOuyUPo.png
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G.Patton

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Was wondering if the 5F-SGT-151 could be crafted and instead of 1-bromo-5-fluoropentane used as tail,
we could use 1-bromo-6-fluorohexane. Would this give us even bigger receptor affinity / effects?
BackstagePantherAccording to this data, I would say yes, but it's just a hypothesis.
 
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Lordseeds

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Yes, I think that will be enough. I have another question. Which is the strongest cannabinoids?
 

king of synthesis

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Reaction scheme:
View attachment 3065
Synthesis:
1. A solution of 1H-pyrrolo[2, 3-b]pyridine-3-carboxylic acid (0.49 g, 3 mmol), oxalyl chloride (0.6 mL, 7.2 mmol), and DMF (1 mL) in dichloromethane (20 mL) was stirred for 20 min.
2. The mixture was evaporated and then redissolved in methanol (20 mL) and stirred for 40 min.
3. The mixture was evaporated and then extracted with ethyl acetate.
4. The organic phase was washed with saturated sodium bicarbonate solution and dried with Na2SO4, and the solvent was removed in vacuo to yield the white solid (0.36 g, 68%).
5. A solution of Step 4 (0.36 g, 2 mmol), potassium t-butoxide (0.27 g, 2.4 mmol), and 1-bromo-5-fluoropentane (1.6 g,9.5 mmol) in THF (20 mL) was stirred for 24 h.
6. The mixture was extracted with ethyl acetate.
7. The organic phase was washed with brine and dried with Na2SO4, and the solvent was removed in vacuo.
8. The residue was purified by silica gel chromatography with stepwise gradient elution of n-hexane/ethyl acetate (3:1–2:1–1:1, v/v) to yield the white solid (0.35 g, 65%).
9. A solution of step 8 (0.35 g, 1.3 mmol) and 6 mol/L sodium hydroxide solution (10 mL) in methanol/THF (2:1,v/v, 15 mL) was stirred for 1.5 days.
10. The mixture was evaporated, added to water, and then washed with ethyl acetate.
11. A solution of 1 mol/L hydrochloric acid was added to the aqueous phase, and the mixture was extracted with ethyl acetate.
12. The organic phase was washed with brine and dried with Na2SO4, and the solvent was removed in vacuo to yield the white solid (0.39 g, quant.)
13. A solution of step 12 (0.39 g, 1.3 mmol), oxalyl chloride (3 mmol), and DMF (1 mL) in dichloromethane (12 mL) was stirred for 10 min.
14. The mixture was evaporated and then redissolved in dichloromethane (10 mL).
15. Cumylamine (2 mmol) and triethylamine (0.5 mL) were added to the solution and stirred for 15 h.
16. The mixture was evaporated and then extracted with ethyl acetate.
17. The organic phase was washed with 0.1 mol/L hydrochloric acid solution, saturated sodium bicarbonate solution and brine, and then dried with Na2SO4, and the solvent was removed in vacuo to yield the white solid (0.37 g, 77%).
William DampierHallo,
Is pyridine alternative to potassium tert butoxide in this reaction?
 
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