Potassium Carbonate → HCID 68588703, compound

HRID 1047782Notes

Reaction equation

HRID 1047782 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]\[CH3:28].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][CH3:28])[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 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 593141532-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 68588703HCID 68588703, compoundYield 63%

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 (600 mg, 1.34 mmol) and trans-1-propen-1-ylboronic acid (460 mg, 5.36 mmol) in EtOH (10 mL) and dioxane (10 mL) is added palladium anchored homogeneous catalyst, FibreCatPd(0), (4.84% Pd, 285 mg, 0.13 mmol) and 2M aqueous solution of K2SO4 (2.68 mL, 5.36 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 and gave the pure product (142) as white solid (300 mg, 63%).

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-f242e0d44f5d458cb1dd68b2b6b3b8de
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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