Toluene → 5-Chloro-2-methyl-3-(8-quinolinyl)-1H-indole-1-acetic acid

HRID 418455

Reaction equation

HRID 418455 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](B(O)O)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:14](=[O:17])(O)[O-:15].[Na+].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-:26].[Li+]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Pd].[Pd].[Pd].C(O)C>[Cl:26][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:1]([CH2:10][C:14]([OH:15])=[O:17])[C:2]([CH3:3])=[C:25]2[C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 21886457Quinoline-7-boronic acid

Product 1

HCID 103832715-Chloro-2-methyl-3-(8-quinolinyl)-1H-indole-1-acetic acid

Reagents, catalysts & solvents 2

HCID 86600928Tetrakis palladium triphenylphosphineCatalystHCID 702EthanolSolvent

Procedure

The product of part b (250 mg), 7-quinoline boronic acid (114 mg), 2M sodium bicarbonate (0.7 ml), toluene, ethanol, tetrakis palladium triphenyl phosphine (O) and lithium chloride were heated at reflux for 2 hours. The reaction mixture was concentrated in vacuo, purified using amine resin and then by reverse phase preparative HPLC to give the title compound as a white solid.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-fd2c68541ba04a9aa2532959621190bc
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Linked notes

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