Indole-3-Carboxaldehyde → HCID 20109664, compound

HRID 1843989Notes

Reaction equation

HRID 1843989 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.Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[H-].[Na+]>CN(C=O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH:10]=[O:11])=[CH:2]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 20109664HCID 20109664, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using analogous procedure as those described to prepare intermediate I-38b, 1H-Indole-3-carbaldehyde (10 g, 68.96 mmol) was reacted with 1-(chloromethyl)-4-methoxybenzene (11.26 mL, 82.75 mmol) and 60% NaH (5.5 g, 137.92 mmol) in DMF (140 mL) at room temperature for 1 hour to afford 20 g of the product.

Workup

  1. customto prepare intermediate I-38b

Sources & evidence

ORD record
ord-b4599093432c4ce49f14b0885186aec9
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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