Indole-3-Carboxaldehyde → HCID 131732019, compound

HRID 337608Notes

Reaction equation

HRID 337608 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:21]([O:20][C:19](=[O:25])[NH:18][CH2:17][CH2:16][CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydrideHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 131732019HCID 131732019, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Indole-3-carbaldehyde (1 eq.) was dissolved in DMF (0.15 M). Sodium hydride was added (1.3 eq.) and the resulting solution was stirred at RT for 20 min. Tetrabutylammonium iodide (1 eq.) and tert-butyl 3-bromopropylcarbamate (2 eq.) were then added and the reaction solution was allowed to stir at RT for 18 h. The reaction mixture was subsequently quenched with sat. aq. NH4Cl and extracted with EtOAc. The combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a light pink solid.

Workup

  1. stirringto stir at RT for 18 h
  2. customThe reaction mixture was subsequently quenched with sat. aq. NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationFiltration and concentration of the filtrate in vacuo
  6. customafforded a yellow oil
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-f3db5ca5546747cd8096b30b94ceef06
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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