Carbon Dioxide → 5-Carboxy-2-ethylindole

HRID 2288798Notes

Reaction equation

HRID 2288798 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.CC1NC2C(C=1)=CC=CC=2.Cl[C:23]1NC2C(C=1)=CC=CC=2.[C:32](=[O:34])=[O:33]>>[C:32]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH3:23])=[CH:5]2)([OH:34])=[O:33]

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 72242-MethylindoleHCID 706365-Chloro-2-methylindoleHCID 6408402-chloro-1H-indole

Product 1

HCID 227083285-Carboxy-2-ethylindole

Procedure

This synthesis could start with 5-chloro-2-methylindole, which could be alkylated with methyl indole (see 28a). The product chloroindole could then be converted to its Grignard species and exposed to carbon dioxide to finish the synthesis.

Workup

  1. customThis synthesis
  2. customthe synthesis

Sources & evidence

ORD record
ord-da32abe4ec5c4fc4a25d1efda5115b68
Source dataset
uspto-grants-2000_07
Patent number
US06090838

Reaction notes

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