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

HRID 589334Notes

Reaction equation

HRID 589334 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:8]2[CH3:21])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[C:41](Cl)=[O:42].C(=O)(O)[O-].[Na+]>ClCCl>[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[C:41]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:8]2[CH3:21])=[CH:4][CH:3]=1)=[O:42]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 516892Sodium BicarbonateHCID 89590248methyl 2-[1-(4-aminobenzyl)-2-methyl-1H-indol-3-yl]acetate

Product 1

HCID 89590251methyl 2-[1-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-3-yl]acetateYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a dry reaction vessel, methyl 2-[1-(4-aminobenzyl)-2-methyl-1H-indol-3-yl]acetate (260 mg, 0.843 mmol) was added, and dissolved in 10 mL dichloromethane. Triethylamine (0.36 mL, 2.59 mmol) was added, and 2-naphthoyl chloride (195 mg, 1.02 mmol) was added slowly in an ice bath. Upon completion of addition, it was reacted for 1 h in an ice bath, and stirred at room temperature for 3 days. An aqueous solution of sodium bicarbonate was added to quench. It was extracted with dichloromethane, rotate evaporated to dryness, chromatographed on a column to obtain a white solid 150 mg, at a yield of 38.4%.

Workup

  1. additionwas added
  2. additionUpon completion of addition, it
  3. customwas reacted for 1 h in an ice bath
  4. customto quench
  5. extractionIt was extracted with dichloromethane, rotate
  6. customevaporated to dryness
  7. customchromatographed on a column

Sources & evidence

ORD record
ord-edc498c97eb34b11840112124adf1e7e
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

Loading…