Water → ethyl 2-[3-[4-(2-naphthamido)benzyl]-2-ethyl-1H-indol-1-yl]acetate

HRID 589357Notes

Reaction equation

HRID 589357 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][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[CH2:22][CH3:23])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[C:43](Cl)=[O:44].O>ClCCl>[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[C:43]([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[CH2:22][CH3:23])=[CH:24][CH:25]=1)=[O:44]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 89590280ethyl 2-[3-(4-aminobenzyl)-2-ethyl-1H-indol-1-yl]acetate

Product 1

HCID 89590278ethyl 2-[3-[4-(2-naphthamido)benzyl]-2-ethyl-1H-indol-1-yl]acetateYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a dry reaction vessel, ethyl 2-[3-(4-aminobenzyl)-2-ethyl-1H-indol-1-yl]acetate (288 mg, 0.86 mmol) was added, and dissolved in 7 mL dichloromethane. Triethylamine (0.36 mL, 2.59 mmol) was added, in an ice bath a dichloromethane solution 2 mL dissolving 2-naphthoyl chloride (163 mg, 0.86 mmol) was added slowly. After completion of dropwise addition, it was reacted in an ice bath for 1 h, and stirred at room temperature overnight. Water was added into the system, extracted with dichloromethane, rotate evaporated to dryness to obtain a crude. It was washed again with a small amount of acetonitrile to obtain the yellow product 340 mg, at a yield of 80.2%.

Workup

  1. additionwas added
  2. additionwas added slowly
  3. additionAfter completion of dropwise addition, it
  4. customwas reacted in an ice bath for 1 h
  5. extractionextracted with dichloromethane, rotate
  6. customevaporated to dryness
  7. customto obtain a crude
  8. washIt was washed again with a small amount of acetonitrile

Sources & evidence

ORD record
ord-cea2504a28914e6d83fad57fec7d9c52
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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