Carbon Dioxide → 1-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole-5-carboxylic acid

HRID 36896Notes

Reaction equation

HRID 36896 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[S:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.C([Li])CCC.[C:25](=[O:27])=[O:26]>C1COCC1>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:25]([OH:27])=[O:26])=[CH:10][CH:9]=2)[C:5]([S:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:6]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 19936624HCID 19936624, compoundHCID 178418339Butyllithium

Product 1

HCID 199366641-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-1-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole (19 g, prepared in Example 58) in THF (100 ml) is treated at -78° C. with a solution of butyllithium (31.5 ml, 2.5M in hexane). After 1 hour at this temperature, carbon dioxide is passed into the solution until it is saturated. After one hour, the reaction mixture is left to return to room temperature. The solvent is evaporated off and the residue is taken up with ether to give 1-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole-5-carboxylic acid (22.8 g) in the form of a yellow solid, which is used for the next step without purification.

Workup

  1. waitthe reaction mixture is left
  2. customto return to room temperature
  3. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-1f17195807d04142a0764a98cbb30cf2
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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