Indole → HCID 22349913, compound

HRID 1698802Notes

Reaction equation

HRID 1698802 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., and the reaction mixture is heated to reflux temperature with stirring for 3 hours and allowed to stand overnight at room temperature. The precipitate is filtered and 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 temperature
  6. filtrationThe precipitate is filtered
  7. additiontreated with water
  8. customthe dried compound is purified on a silica gel column (silica gel 60, Merck AG, Darmstadt)

Sources & evidence

ORD record
ord-18a5cf768950459bb3e93609edd96653
Source dataset
uspto-grants-2002_02
Patent number
US06344467B1

Reaction notes

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