Carbon Dioxide → 5-Carboxy-2-ethylindole

HRID 1978989Notes

Reaction equation

HRID 1978989 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-0a5a880e4f0e4d61ac2e74389dd3f109
Source dataset
uspto-grants-2001_05
Patent number
US06239161B1

Reaction notes

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