Jwh 250 → 2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone

HRID 61307Notes

Reaction equation

HRID 61307 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:13]=1)=[O:11]>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:13]=1)=[O:11]

Participants

3

Reactant 1

HCID 44397540Jwh 250

Product 1

HCID 866910902-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanoneYield 29.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(2-Methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (JWH-250) 4 (3 g, 8.94 mmol) was dissolved in anhydrous dichloromethane (40 ml) and cooled at −78° C. A solution of 1NBBr3 (9.83 ml, 9.83 mmol) was added dropwise and once the addition was complete the reaction mixture was allowed to warm up to room temperature and was stirred at room temperature overnight. The reaction mixture was poured into a solution of 2NHCl (100 ml) and stirred for 30 min, then extracted three times with dichloromethane (3×150 ml) and the combined organic fractions dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 0%-20% ethyl acetate in hexane) to give 840 mg (29%) of 2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (O-desmethyl JWH-250) 5 as a solid.

Workup

  1. additionA solution of 1NBBr3 (9.83 ml, 9.83 mmol) was added dropwise
  2. additiononce the addition
  3. temperatureto warm up to room temperature
  4. additionThe reaction mixture was poured into a solution of 2NHCl (100 ml)
  5. stirringstirred for 30 min
  6. extractionextracted three times with dichloromethane (3×150 ml)
  7. dry with materialthe combined organic fractions dried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 0%-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-344a8cb10cd14784be1c49bc42103ae5
Source dataset
uspto-grants-2016_09
Patent number
US09441033B2

Reaction notes

Loading…