Pyridine → HCID 21477616, compound

HRID 2293770Notes

Reaction equation

HRID 2293770 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.N1C=CC=CC=1.[Cl:22][CH2:23][CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl.C1COCC1.C(Cl)(Cl)Cl>[Cl:22][CH2:23][CH2:24][CH2:25][S:26]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2)(=[O:28])=[O:27]

Participants

7

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylate

Product 1

HCID 21477616HCID 21477616, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-aminoindole-2-carboxylate (2.0 g) and pyridine (0.82 ml) are dissolved in 15 ml of methylene chloride and 10 ml of THF. Then the reaction is cooled to 0° and 3-chloropropanesulfonyl chloride (1.25 ml) is added and the reaction is allowed to slowly warm to 20°-25° and stir for 16 hr. Then the reaction is diluted with chloroform, washed with saturated aqueous sodium bicarbonate and saline. The organic layers are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product is dissolved in ethyl acetate and filtered through a plug of silica gel and crystallized from methanol, mp 195°-196°.

Workup

  1. temperatureThen the reaction is cooled to 0°
  2. temperatureto slowly warm to 20°-25°
  3. washwashed with saturated aqueous sodium bicarbonate and saline
  4. dry with materialThe organic layers are dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe product is dissolved in ethyl acetate
  7. filtrationfiltered through a plug of silica gel
  8. customcrystallized from methanol, mp 195°-196°

Sources & evidence

ORD record
ord-5296720de9c24931bf7a8d9b93a9e135
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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