Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate → Methyl 6-chloro-1H-indole-5-carboxylate

HRID 1023152Notes

Reaction equation

HRID 1023152 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[C:13][Si](C)(C)C)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:18])[CH:3]=1>CN(C=O)C.[Cu]I>[Cl:18][C:4]1[CH:3]=[C:2]2[C:11]([CH:12]=[CH:13][NH:1]2)=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 59625799Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate

Product 1

HCID 10727132Methyl 6-chloro-1H-indole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of compound 70p (0.532 mmol, 150 mg) and CuI (0.32 mmol, 60 mg) in DMF (1.5 mL) was heated at 110° C. for 5 h and them cooled to room temperature. The reaction was quenched with water and extracted with EtOAc. The organic layer was concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 70q.

Workup

  1. temperaturethem cooled to room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified by flash column chromatography (silica gel, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ebea2849a7804b7a9e36464a98a90f9c
Source dataset
uspto-grants-2014_05
Patent number
US08722658B2

Reaction notes

Loading…