Carbon Dioxide → 5-Carboxy-2-ethylindole

HRID 1956550Notes

Reaction equation

HRID 1956550 reaction equation
ClC1C=C2C(=CC=1)NC(C)=C2.CC([CH2:15][CH2:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)=C.ClC1NC2C(C=1)=CC=CC=2.[C:36](=[O:38])=[O:37]>>[C:36]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH2:16][CH3:15])=[CH:25]2)([OH:38])=[O:37]

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 706365-Chloro-2-methylindoleHCID 6408402-chloro-1H-indoleHCID 187616282-(2-Methyl-1-buten-4-yl)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-abda413fe31542eba4950c0b6f1bf4c6
Source dataset
uspto-grants-1998_07
Patent number
US05780496

Reaction notes

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