Triethylamine → ethyl 2-[3-[4-(3,4-dichlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetate

HRID 589343Notes

Reaction equation

HRID 589343 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]=2[CH3:22])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[Cl:42])[C:36](Cl)=[O:37]>ClCCl>[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[Cl:42])[C:36]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]=2[CH3:22])=[CH:23][CH:24]=1)=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 89590249HCID 89590249, compound

Product 1

HCID 90449168ethyl 2-[3-[4-(3,4-dichlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetateYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a dry reaction vessel, ethyl 2-[3-(4-aminobenzyl)-2-methyl-1H-indol-1-yl]acetate (1.0 g, 3.11 mmol) was added, and dissolved in 15 mL dichloromethane. Triethylamine (1.3 mL, 9.3 mmol) was added, and in an ice bath a dichloromethane solution dissolving 3,4-dichlorobenzoyl chloride (0.652 g, 3.11 mmol) was added slowly. After completion of dropwise addition, it was reacted in an ice bath for 4 h, and filtered. An aqueous solution of sodium bicarbonate was added, extracted with dichloromethane, rotate evaporated to dryness, chromatographed on a column to obtain a white solid 1.23 g, at a yield of 79.7%.

Workup

  1. additionwas added
  2. additionwas added slowly
  3. additionAfter completion of dropwise addition, it
  4. customwas reacted in an ice bath for 4 h
  5. filtrationfiltered
  6. additionAn aqueous solution of sodium bicarbonate was added
  7. extractionextracted with dichloromethane, rotate
  8. customevaporated to dryness
  9. customchromatographed on a column

Sources & evidence

ORD record
ord-c33858cafd574c6cb1422cb5f902ca51
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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