2-Chloropyridine → HCID 22277752, compound

HRID 1955674Notes

Reaction equation

HRID 1955674 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[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN1CCCC1=O>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 6432211-AminoindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 22277752HCID 22277752, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Potassium tert-butoxide (3.4 g) was added to a room temperature solution of N-aminoindole (2.0 g) in 1-methyl-2-pyrrolidinone (40 ml). After stirring for one hour, 2-chloropyridine (1.6 ml) was added and the resulting solution was stirred for forty-eight hours. The reaction mixture was then quenched with water, diluted with ethyl acetate (250 ml) and washed with brine (3×250 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give an oil. Purification of the residue by flash chromatography (silica, 0-5% ethyl acetate/dichloromethane) gave the title compound as a solid (2.0 g), m.p. 109°-110° C.

Workup

  1. stirringthe resulting solution was stirred for forty-eight hours
  2. customThe reaction mixture was then quenched with water
  3. additiondiluted with ethyl acetate (250 ml)
  4. washwashed with brine (3×250 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 residue by flash chromatography (silica, 0-5% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-70f2173d38794e97825135364f862412
Source dataset
uspto-grants-1998_07
Patent number
US05776955

Reaction notes

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