Carbon Dioxide → 5-methoxy-1H-indole-7-carboxylic acid

HRID 661339Notes

Reaction equation

HRID 661339 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[Li]CCCC.[C:18](=[O:20])=[O:19]>C1COCC1.CCCCCC>[CH3:12][O:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([C:18]([OH:20])=[O:19])[CH:3]=1)[NH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 198041607-Bromo-5-methoxy-1H-indoleHCID 178418339Butyllithium

Product 1

HCID 597466045-methoxy-1H-indole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 7-Bromo-5-methoxy-1H-indole (described in WO 2002028861) in THF was treated with 2 eq. of a solution of n-BuLi in n-hexane (1.6M) at 5° and after 30 min at this temperature was cooled to −75°. Dry ice (excess) was added and after 15 mins the mixture was quenched with H2O and washed with EtOAc. After acidification of the aqueous layer and extraction into CH2Cl2, evaporation gave the desired product.

Workup

  1. temperaturewas cooled to −75°
  2. customwas quenched with H2O
  3. washwashed with EtOAc
  4. extractionAfter acidification of the aqueous layer and extraction
  5. custominto CH2Cl2, evaporation

Sources & evidence

ORD record
ord-5b555b3220984de8a2f53c54beac1c55
Source dataset
uspto-grants-2011_12
Patent number
US08084609B2

Reaction notes

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