Triethylamine → HCID 21460717, compound

HRID 2082486Notes

Reaction equation

HRID 2082486 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH2:16](N(CC)CC)C.[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28].C(OCC)(=O)C>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](=[O:28])[CH2:16][NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 743763-Fluorobenzoyl chlorideHCID 15337900HCID 15337900, compound

Product 1

HCID 21460717HCID 21460717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Suspend the 3-amino-2-carbmethoxy-6-chloroindole (1 g, 4.45 mmol) in methylene chloride (50 mL) and add triethylamine (0.416 mL, 4.6 mmol) to produce a mostly clear solution. Add the m-fluorobenzoyl chloride (0.561 mL, 4.6 mmol) and stir for five minutes at room temperature to produce a thick white precipitate. Dilute the reaction with ethyl acetate (700 mL), rinse with water, dry over magnesium sulfate, filter and concentrate in vacuo to 300 mL. Recrystallize by adding hot hexane (150 mL) to the already hot solution of ethyl acetate to yield the title compound.

Workup

  1. customto produce a mostly clear solution
  2. customto produce a thick white precipitate
  3. additionDilute
  4. washrinse with water
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo to 300 mL
  8. customRecrystallize
  9. additionby adding hot hexane (150 mL) to the already hot solution of ethyl acetate

Sources & evidence

ORD record
ord-540e2c44999b40329ef7a8a7b84145c5
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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