Sodium hydride → HCID 67086824, compound

HRID 2365567Notes

Reaction equation

HRID 2365567 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][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O: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][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 67086824HCID 67086824, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion in mineral oil, 86 mg, 2.14 mmol) is added to a solution of methyl indole-4-carboxylate (250 mg, 1.427 mmol) in DMF (20 ml) and the resulting suspension is stirred at room temperature for 30 minutes. After this time (2-(2-bromoethoxy)tetrahydro-2H-pyran (388 mg, 1.86 mmol) is added and the reaction is stirred at room temperature for 22 hours. Dilution with EtOAc (50 ml), washing with water (25 ml×3), saturated NaHCO3 (25 ml×2) and brine (25 ml), drying over MgSO4, concentration in vacuo and purification by chromatography (SiO2, DCM/MeOH) affords 1-[2-(Tetrahydro-pyran-2-yloxy)-ethyl]-1H-indole-4-carboxylic acid methyl ester; [M+H]+ 304

Workup

  1. stirringthe reaction is stirred at room temperature for 22 hours
  2. washDilution with EtOAc (50 ml), washing with water (25 ml×3), saturated NaHCO3 (25 ml×2) and brine (25 ml)
  3. dry with materialdrying over MgSO4, concentration in vacuo and purification by chromatography (SiO2, DCM/MeOH)

Sources & evidence

ORD record
ord-46d8a474c2ca4fa0a2ac24b05a941c0a
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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