(Cyclopent-1-en-1-yl)boronic acid → 2-(2-Cyclopent-1-enyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047772Notes

Reaction equation

HRID 1047772 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].[C:26]1(B(O)O)[CH2:30][CH2:29][CH2:28][CH:27]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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[C:26]2[CH2:30][CH2:29][CH2:28][CH:27]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 593141532-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593141462-(2-Cyclopent-1-enyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (800 mg, 1.78 mmol) and cyclopenten-1-ylboronic acid (796 mg, 7.11 mmol) in dioxane (20 mL) is added Pd(PPh3)4 (412 mg, 0.36 mmol) and 2M aqueous solution of CsCO3 (5.34 mL, 10.7 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 2.7 h. After concentration in vacuo, the residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-40% EtOAc in heptane) to give a pure product (131) as a brown solid (589 mg, 85%).

Workup

  1. customThe resulting reaction mixture
  2. customrun in a microwave reaction
  3. custom110° C., 2.7 h
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-e38c089094be48fd9f1aedf19714b8d0
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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