HCID 66765609, compound → HCID 66764894, compound

HRID 1466915Notes

Reaction equation

HRID 1466915 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=2)=[C:9]1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66765609HCID 66765609, compound

Product 1

HCID 66764894HCID 66764894, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

1-Benzyl-3-(3-bromo-phenylsulfanyl)-6-chloro-1H-indole-2-carboxylic acid (from the previous step) was dissolved in quinoline (5 mL) then copper (0.120 g, 2 mmol) was added and the reaction was placed in the microwave for 10 minutes at 150° C., and this heating was repeated 3 additional times. The reaction was submitted to standard workup procedures then purified by silica gel chromatography (0-20% EtOAc in hexanes) to provide the title compound.

Workup

  1. customthen purified by silica gel chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-625d46077e1d4f3b82b5251f27afe798
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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