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

HRID 589351Notes

Reaction equation

HRID 589351 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:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1>ClCCl>[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][C:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]=3[CH3:22])=[CH:23][CH:24]=2)=[O:38])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 89590249HCID 89590249, compound

Product 1

HCID 90449096ethyl 2-[3-[4-(4-chlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetateYield 40.6%

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, 3.10 mmol) was added, and dissolved in 15 mL dichloromethane. Triethylamine (1.3 mL, 9.34 mmol) was added, in an ice bath a dichloromethane solution dissolving 4-chlorobenzoyl chloride (0.544 g, 3.11 mmol) was added slowly. After completion of dropwise addition, it was reacted in an ice bath for 4 h. It was 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 0.580 g, at a yield of 40.6%.

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. filtrationIt was filtered
  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-8e9679c7de3a41129272965a25b44961
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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