1,4-Dibromobutane → 5-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl ester

HRID 1633626Notes

Reaction equation

HRID 1633626 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:28][CH2:27][CH2:26][CH2:25][Br:24])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 22596220N-Boc-5-Hydroxyindole

Product 1

HCID 695484135-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl esterYield 75.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
100 °C

Procedure

6.07 g (26 mmol) 5-Hydroxy-indole-1-carboxylic acid tert-butyl ester in 10 ml acetone were treated with 13.8 g (100 mmol) powdered K2CO3 and 11.8 ml (100 mmol) 1,4-dibromobutane. The suspension was stirred at 100° C. for 3 h, cooled to RT, and acetone was added. The suspension was filtered and concentrated. The residue was redissolved in ether and 0.5 M HCl, the inorganic phase was extracted with ether and the combined organic phases were washed with water, and dried over Na2SO4. Column chromatography on silica gel with a gradient hexane to hexane/EtOAc 19:1 yielded 7.2 g (65%, 3 steps) 5-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl ester as colorless oil, MS: 367 (M, 1Br).

Workup

  1. temperaturecooled to RT
  2. filtrationThe suspension was filtered
  3. concentrationconcentrated
  4. dissolutionThe residue was redissolved in ether
  5. extraction0.5 M HCl, the inorganic phase was extracted with ether
  6. washthe combined organic phases were washed with water
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-b1c2d94478784747b6f341c3eabbac13
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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