Indole → HCID 22349913, compound

HRID 2105508Notes

Reaction equation

HRID 2105508 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10](Cl)(=[O:14])[C:11](Cl)=[O:12].[NH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>CCOCC.O1CCCC1>[N:20]1[CH:21]=[CH:22][C:17]([NH:16][C:10](=[O:14])[C:11]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[O:12])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 798IndoleHCID 17274-AminopyridineHCID 65578Oxalyl chloride

Product 1

HCID 22349913HCID 22349913, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10 g (85.3 mmol) of indole in 100 ml of ether is added dropwise at 0° C. to a solution of 9 ml of oxalyl chloride in 100 ml of anhydrous ether. The mixture is kept under reflux for 3 hours. A suspension of 12 g (127.9 mmol) of 4-aminopyridine in 500 ml of tetrahydrofuran is then added dropwise at −5° C., the reaction mixture is heated to reflux temperature with stirring for 3 hours and allowed to stand overnight at room temp. It is filtered, the precipitate is treated with water and the dried compound is purified on a silica gel column (silica gel 60, Merck AG, Darmstadt) using the eluent methylene chloride/ethanol (10:1, v/v).

Workup

  1. temperatureunder reflux for 3 hours
  2. additionis then added dropwise at −5° C.
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux temperature
  5. waitto stand overnight at room temp
  6. filtrationIt is filtered
  7. additionthe precipitate is treated with water
  8. customthe dried compound is purified on a silica gel column (silica gel 60, Merck AG, Darmstadt)

Sources & evidence

ORD record
ord-d5ee423f2cfa4b888bb16e5d9dc5fe7c
Source dataset
uspto-grants-2009_08
Patent number
US07579365B2

Reaction notes

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