Indole → Indole-2-carboxaldehyde

HRID 250187Notes

Reaction equation

HRID 250187 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[N+](C)=CCl.[Cl-].C(Cl)(=O)[C:17](Cl)=[O:18]>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 798IndoleHCID 65578Oxalyl chlorideHCID 77311Chloro-N,N-dimethylformiminium chloride

Product 1

HCID 96389Indole-2-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In Step 1 of Scheme F, indole compound a is treated with the Vilsmeier reagent formed by mixing oxalyl chloride with dimethyl formamide to form indole aldehyde w, which in turn is reacted with Meldrum's acid in Step 2 to yield indole compound x. Indole x is then treated with Grignard reagent y in Step 3 to afford indole compound z. In Step 4 compound z is reacted with amine d in the presence of pyridine to give indole amide r, which is then reduced in Step 5 to provide aminopropyl indole compound s. Compound s is a compound of formula I in accordance with the invention.

Workup

  1. customformed

Sources & evidence

ORD record
ord-c1ea5e37b9ab4ac1860f7363f7ba9ad6
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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