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

HRID 2038437Notes

Reaction equation

HRID 2038437 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 22m (150 mg, 0.532 mmol) and CuI (60 mg, 0.32 mmol) 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 22n.

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-904fcfac9af345018361c269a6c1c995
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

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