Triethylamine → HCID 21460715, compound

HRID 2396362Notes

Reaction equation

HRID 2396362 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=2[Cl:11])[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18](N(CC)CC)C.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29].C(OCC)(=O)C>C(Cl)Cl>[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](=[O:29])[CH2:18][NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=2[Cl:11])[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 98082-Fluorobenzoyl chlorideHCID 15043966HCID 15043966, compound

Product 1

HCID 21460715HCID 21460715, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (1.09 g, 4 mmol) in methylene chloride (25 mL) and add triethylamine (0.578 mL, 4 mmol) followed by o-fluorobenzoyl chloride (1 g, 4 mmol). Stir the reaction for 1 hour at room temperature. Add an additional amount of methylene chloride(25 mL) and stir overnight. Dilute the reaction with ethyl acetate (100 mL), wash with water (100 mL) and dry the organic phase. Concentrate in vacuo and recrystallize the residue from ethyl acetate/hexane to yield thetitle compound (1.05 g, 67%); mp >290° C.

Workup

  1. customthe reaction for 1 hour at room temperature
  2. stirringstir overnight
  3. additionDilute
  4. washwash with water (100 mL)
  5. customdry the organic phase
  6. concentrationConcentrate in vacuo
  7. customrecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0de23a6d182a4f58add26885e3ea361e
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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