Triethylamine → HCID 21460722, compound

HRID 2396365Notes

Reaction equation

HRID 2396365 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:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30].C(OCC)(=O)C>C(Cl)Cl>[F:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](=[O:30])[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 743763-Fluorobenzoyl chlorideHCID 15043966HCID 15043966, compound

Product 1

HCID 21460722HCID 21460722, compoundYield 81%

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 m-fluorobenzoyl chloride (0.488 mL, 4 mmol). Stir the reactionfor 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 the title compound (1.28 g, 81%); mp 234°-235° C.

Workup

  1. stirringstir overnight
  2. additionDilute
  3. washwash with water (100 mL)
  4. customdry the organic phase
  5. concentrationConcentrate in vacuo
  6. customrecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-06c69f9577954daa9e22a221be4b7289
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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