Carbon Dioxide → HCID 12230326, compound

HRID 855284Notes

Reaction equation

HRID 855284 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH3:11])=[CH:7]2.[Li]CCCC.[C:17](=[O:19])=[O:18].O>C1COCC1.CCCCCC>[CH3:11][C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 44130817-Bromo-2-methylindoleHCID 178418339Butyllithium

Product 1

HCID 12230326HCID 12230326, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
2.5 °C

Procedure

1000 mg of 7-bromo-2-methyl-indole (4.8 mmol) were dissolved in 15 ml THF and 8.9 ml of a 1.6 molar solution of n-BuLi in hexane were added at −78° C. The reaction mixture was then allowed to warm to 0-5° C. and was stirred at this temperature for 30 min. Then it was cooled again to −78° C., dry ice was added and the mixture was allowed to warm to rt. After 15 min at rt it was poured into water and extracted twice with ether. The aqueous phase was then acidified with 1 N HCl solution and extracted several times with DCM. The combined DCM extracts were then dried with magnesium sulfate, filtered and the solvent was evaporated. The remaining residue was triturated with pentane. Final filtration yielded 157 mg (31%) of 2-methyl-1H-indole-7-carboxylic acid as an off-white solid. MS (ISP) 174.3 (M−H)−.

Workup

  1. temperatureThen it was cooled again to −78° C.
  2. temperatureto warm to rt
  3. extractionextracted twice with ether
  4. extractionextracted several times with DCM
  5. dry with materialThe combined DCM extracts were then dried with magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe remaining residue was triturated with pentane
  9. filtrationFinal filtration

Sources & evidence

ORD record
ord-9bb3c9e942174166ad9c08e81dbe5e5f
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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