4-Chloropyridine hydrochloride → 3-(4-Pyridinylamino)-1H-indole-2-carboxylic acid ethyl ester

HRID 1728613Notes

Reaction equation

HRID 1728613 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl.Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>CN1CCCC1=O>[N:21]1[CH:22]=[CH:23][C:18]([NH:1][C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 818524-Chloropyridine hydrochlorideHCID 732887Ethyl 3-amino-1H-indole-2-carboxylate

Product 1

HCID 104689203-(4-Pyridinylamino)-1H-indole-2-carboxylic acid ethyl esterYield 60.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution ethyl 3-aminoindole-2-carboxylate (4.94 g, 24.2 mmole) and 4-chloropyridine hydrochloride (3.63 g, 24.2 mmole) in 70 mL of 1-methyl-2-pyrrolidinone was heated at 165° C. for 6 hours. The reaction mixture was then quenched into water and the aqueous phase was washed with ethyl acetate. After basification with a potassium carbonate solution, a solid was filtered, rinsed with water and ether and dried to give 4.13 g of a brown solid. A 2.2 g portion was recrystallized from methanol (charcoal treatment) to give 1.40 g of an off-white solid, mp: 248°-250° C. (dec.)

Workup

  1. customThe reaction mixture was then quenched into water
  2. washthe aqueous phase was washed with ethyl acetate
  3. filtrationAfter basification with a potassium carbonate solution, a solid was filtered
  4. washrinsed with water and ether
  5. customdried

Sources & evidence

ORD record
ord-29c07b7f09324a3dab40fba91cf5713d
Source dataset
uspto-grants-1994_07
Patent number
US05328920

Reaction notes

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