Water → HCID 21107343, compound

HRID 1752211Notes

Reaction equation

HRID 1752211 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:15]([Cu])#[N:16].O>CN1CCCC1=O>[CH:4]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[C:2]([C:15]#[N:16])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2524463-BromocarbazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 21107343HCID 21107343, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-bromo-9H-carbazole (123.4 mg, 0.50 mmol) and CuCN (49.9 mg, 0.56 mmol) in N-methyl-pyrrolidone (2 mL) was heated at 200° C. for 5 h. The cooled reaction mixture was poured into water and the precipitate was filtered and washed with ethyl acetate. The filtrate was extracted with ethyl acetate and the combined ethyl acetate extracts were washed with water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to afford the product as a white solid (84.7 mg, 88%).

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe precipitate was filtered
  3. washwashed with ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe combined ethyl acetate extracts were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-6dffb15773e246c2aee414153fbda7e2
Source dataset
uspto-grants-2015_10
Patent number
US09162980B2

Reaction notes

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