Bromine → 2-(5-Bromo-6-hydroxy-2-naphthyl)-3-pentyl-1H-indole

HRID 495499Notes

Reaction equation

HRID 495499 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[NH:13][C:14]3[C:19]([C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:5]2.CC([O-])=O.[K+].[Br:31]Br>CC(O)=O.O>[Br:31][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:12]1[NH:13][C:14]3[C:19]([C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8]2

Participants

6

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 223273352-(6-Hydroxy-2-naphthyl)-3-pentyl-1H-indole

Product 1

HCID 223273382-(5-Bromo-6-hydroxy-2-naphthyl)-3-pentyl-1H-indoleYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of 2-(6-hydroxy-2-naphthyl)-3-pentyl-1H-indole (1.27 g, 3.85 mmol) in HOAc (25 mL) at 0° C. was added KOAc (0.453 g, 4.62 mmol). The reaction was stirred at this temperature for 10 min., and then a solution of Br2 (0.218 mL, 4.24 mmol) in HOAc (5 mL) was added dropwise to it over a period of ˜10 min. The reaction mixture was allowed to warm to rt and stirred for 4 h. The reaction mixture was then diluted with H2O (50 mL) and extracted with EtOAc (200 mL). The organic layer was washed with brine (20 mL) and then dried (Na2SO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 30% EtOAc:petroleum ether gradient) to afford the product (0.782 g, 50%) as a solid (inseparable mixture of mono- and di-bromo-substituted analogs which were separated in the next step); monobrominated compound: mass spectrum [(−) ESI], m/z 406/408 (M−H)− and dibrominated analog: mass spectrum [(−) ESI], m/z 486 (M−H)−.

Workup

  1. stirringstirred for 4 h
  2. extractionextracted with EtOAc (200 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentration
  6. customthe residue was purified by the Biotage Flash 40 apparatus (10 to 30% EtOAc:petroleum ether gradient)

Sources & evidence

ORD record
ord-0df7902b4cff47f89dcde1348a435210
Source dataset
uspto-grants-2005_09
Patent number
US06939886B2

Reaction notes

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