Sodium hydride → HCID 67087062, compound

HRID 2365563Notes

Reaction equation

HRID 2365563 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=2[CH:5]=[CH:4]1.Br[CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH3:15][O:14][C:12]([C:7]1[C:6]2[CH:5]=[CH:4][N:3]([CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68526Benzene, (2-bromoethoxy)-HCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 67087062HCID 67087062, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion in mineral oil, 68.5 mg, 1.71 mmol) is added to solution of methyl indole-4-carboxylate (200 mg, 1.142 mmol) in DMF (5 ml) and the resulting suspension is stirred at room temperature for 20 minutes. After this time (2-bromoethoxy)benzene (298 mg, 1.484 mmol) is added and the reaction is stirred at room temperature for 18 hours. Dilution with EtOAc (50 ml) and washing with water (25 ml×2), saturated NaHCO3 (25 ml) and brine (25 ml), drying over MgSO4, concentration in vacuo and purification by chromatography (SiO2, EtOAc/iso-hexane) affords 1-(2-Phenoxy-ethyl)-1H-indole-4-carboxylic acid methyl ester; [M+H]+ 296

Workup

  1. stirringthe reaction is stirred at room temperature for 18 hours
  2. washDilution with EtOAc (50 ml) and washing with water (25 ml×2), saturated NaHCO3 (25 ml) and brine (25 ml)
  3. dry with materialdrying over MgSO4, concentration in vacuo and purification by chromatography (SiO2, EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-67bca9c2658348a78e58d38eaf6e398f
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

Loading…