Dimethylformamide → HCID 59817741, compound

HRID 337582Notes

Reaction equation

HRID 337582 reaction equation
CN(C=O)C.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[O:16])=[CH:7]1.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][O:23][CH3:24]>CCOCC>[CH3:24][O:23][CH2:22][CH2:21][CH2:20][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[O:16])=[CH:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydrideHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 59817741HCID 59817741, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To a DMF (0.1 M) solution of indole-3-carbaldehyde (1 eq) was added sodium hydride (60% (w/w) dispersion in oil, 1.1 eq.) at 0° C. followed by 1-bromo-3-methoxypropane (1.5 eq.). The reaction mixture was stirred at 50° C. for 4 h. The mixture was then diluted with ether, washed with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 1:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification of the crude product
  6. customthus obtained by way of flash chromatography (SiO2, 1:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-5fd8e3ad165d4484a637a54c57cdeed6
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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