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

HRID 589341Notes

Reaction equation

HRID 589341 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.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>ClCCl>[CH3:22][C:8]1[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:10]2[C:15]([C:7]=1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][C:34]([C:33]([F:32])([F:43])[F:44])=[CH:35][CH:36]=3)=[CH:24][CH:23]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 89590249HCID 89590249, compound

Product 1

HCID 89590294ethyl 2-[2-methyl-3-[4-[4-(trifluoromethyl)benzamido]benzyl]-1H-indol-1-yl]acetateYield 74.9%

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, 9.34 mmol) was added, and in an ice bath a dichloromethane solution dissolving 4-trifluoromethylbenzoyl chloride (0.649 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 1.15 g, at a yield of 74.9%.

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-579ab416b769471288450f0f21a302a5
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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