Carbon Dioxide → HCID 19936656, compound

HRID 36893Notes

Reaction equation

HRID 36893 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[C:10]2[S:17][CH:18]1[CH2:23][CH2:22][N:21]([O:24][CH3:25])[CH2:20][CH2:19]1.[C:26](=[O:28])=[O:27].[Cl-].[NH4+]>O1CCCC1>[CH3:25][O:24][N:21]1[CH2:22][CH2:23][CH:18]([S:17][C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:26]([OH:28])=[O:27])[CH:8]=3)[N:12]([CH3:16])[CH:11]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 199366555-bromo-3-[(1-methoxypiperidin-4-yl)thio]-1-methyl-1H-indoleHCID 178418339Butyllithium

Product 1

HCID 19936656HCID 19936656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of butyllithium (7.1 ml, 2.5M in hexane) is added dropwise to 5-bromo-3-[(1-methoxypiperidin-4-yl)thio]-1-methyl-1H-indole (4.5 g, prepared in Example 59) in tetrahydrofuran (45 ml) at -78° C. After 1 hour at this temperature, a stream of CO2 is passed into the solution. After the temperature has risen to 0° C., a solution of ammonium chloride is added. The reaction mixture is concentrated, taken up with ether and washed with water. The organic phase is dried over sodium sulfate and concentrated. The 3-[(1-methoxypiperidin-4-yl)thio]-1-methyl-1H-indole-5-carboxylic acid obtained (1.4 g) is crystallized from a small volume of isopropyl ether.

Workup

  1. customhas risen to 0° C.
  2. concentrationThe reaction mixture is concentrated
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2786a26b4c6a48f5b2cf1a45c04cb579
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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