Sodium Carbonate → 2-(5-pyridin-4-yl-1H-indol-3-yl)ethanol

HRID 1095517Notes

Reaction equation

HRID 1095517 reaction equation
[CH:1]1[C:6](Br)=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][OH:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.[N:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCCC1.O>[N:14]1[CH:19]=[CH:18][C:17]([C:6]2[CH:5]=[C:4]3[C:3](=[CH:2][CH:1]=2)[NH:10][CH:9]=[C:8]3[CH2:11][CH2:12][OH:13])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1229565-Bromo-1H-indole-3-ethanolHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 574751392-(5-pyridin-4-yl-1H-indol-3-yl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromotryptophol (1.05 g, 4.39 mmol; see Table 1 and 2) and pyridine-4-boronic acid (10 mg, 6.59 mmol) were suspended in tetrahydrofuran (65 ml), and Na2CO3 solution (4.65 g, 43.9 mmol) in 44 ml of H2O) were added. Bistriphenylphosphinepalladium dichloride (456.2 mg, 0.65 mmol) was then added. The reaction mixture, which was clear when hot, was boiled at 65° C. for 14 h, while stirring. The course of the reaction was monitored by TLC. For working up, the reaction solution was filtered. The filtrate comprised two phases. The organic phase was separated off. The solvent was distilled off on a rotary evaporator. The viscous residue was purified by flash chromatography [silica gel 60 (45 g); eluent: EtOAc (800 ml)].

Workup

  1. customfor 14 h
  2. filtrationthe reaction solution was filtered
  3. customThe organic phase was separated off
  4. distillationThe solvent was distilled off on a rotary evaporator
  5. customThe viscous residue was purified by flash chromatography [silica gel 60 (45 g); eluent: EtOAc (800 ml)]

Sources & evidence

ORD record
ord-b780589c4cba41268be6613214bec022
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…