Potassium Carbonate → 2-[3-Methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

HRID 1047785Notes

Reaction equation

HRID 1047785 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2I)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH:26](/B(O)O)=[CH:27]\[CH2:28][CH2:29][CH3:30].C([O-])([O-])=O.[K+].[K+]>CCO.O1CCOCC1.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH3:30])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5702651(1E)-(Pent-1-en-1-yl)boronic acidHCID 593141532-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593142302-[3-Methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl esterYield 60.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (200 mg, 0.45 mmol) and trans-1-penten-1-ylboronic acid (205 mg, 1.80 mmol) in EtOH (10 mL) and dioxane (10 mL) is added palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84% Pd, 96 mg, 0.045 mmol) and 2M aqueous solution of K2SO4 (0.90 mL, 1.80 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 8 h. After concentration in vacuo, the residue is purified by HPLC to give a pure product (145) as white solid (107 mg, 60%).

Workup

  1. customThe resulting reaction mixture
  2. customrun in a microwave reaction
  3. custom110° C., 8 h
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-1cb6cb402e1d417abb6364d6bcc4cef8
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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