HCID 68294245, compound → HCID 68294348, compound

HRID 1472776Notes

Reaction equation

HRID 1472776 reaction equation
Br[C:2]1[S:3][C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH3:22])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[CH3:14])[N:6]=1.[C:23]([Cu])#[N:24]>>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([C:23]#[N:24])[S:3][C:4]=2[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH3:22])=[C:8]([CH3:14])[CH:9]=1

Participants

3

Reactant 2

HCID 68294245HCID 68294245, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68294348HCID 68294348, compoundYield 88.8%

Conditions

Temperature
150 °C

Procedure

A round-bottomed flask was charged with 2-Bromo-4,5-bis(4-chloro-2-methylphenyl)thiazole (196 mg, 0.47 mmol) and CuCN (84.2 mg, 0.94 mmol). After degassed, 3 mL of DMF was added. The reaction mixture was heated to 150° C. overnight. After cooled to room temperature, the reaction was quenched with 25 mL of water, and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography to afford 150 mg of product.

Workup

  1. customAfter degassed
  2. addition3 mL of DMF was added
  3. temperatureAfter cooled to room temperature
  4. customthe reaction was quenched with 25 mL of water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1749261d2c2e4d1b8e0fc410c6d493c8
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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