3,5-Dichloropyridine → HCID 19072377, compound

HRID 1955673Notes

Reaction equation

HRID 1955673 reaction equation
CC(C)([O-])C.[K+].[NH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.[Cl:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22](Cl)[CH:23]=1>CN1CCCC1=O>[Cl:17][C:18]1[CH:23]=[C:22]([C:9]2[N:8]([NH2:7])[C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:21]=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 171533,5-DichloropyridineHCID 6432211-AminoindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 19072377HCID 19072377, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Potassium tert-butoxide (12.7) was added to a 0° C. solution of N-aminoindole (6.0 g) in 1-methyl-2-pyrrolidinone (150 ml). After stirring for thirty minutes, 3,5-dichloropyridine (7.5 g) was added and the resulting mixture was stirred at room temperature for five hours. The reaction mixture was quenched with water, diluted with ethyl acetate (500 ml) and washed with brine (3×500 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give an oil. Purification of the oil by flash chromatography (silica, 0-2% methanol/dichloromethane) afforded the title compound (11.1 g), m.p. 154°-156° C.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for five hours
  2. customThe reaction mixture was quenched with water
  3. additiondiluted with ethyl acetate (500 ml)
  4. washwashed with brine (3×500 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customPurification of the oil by flash chromatography (silica, 0-2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-76b655cfcbda4de1ab5875b14ea34d43
Source dataset
uspto-grants-1998_07
Patent number
US05776955

Reaction notes

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