Dimethylformamide → HCID 71721309, compound

HRID 1465747Notes

Reaction equation

HRID 1465747 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[CH:6]=2.[C:13]([Cu])#[N:14].CN(C=O)C>C(Cl)Cl>[Cl:12][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([C:13]#[N:14])[CH:3]=[N:4]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 145559333-Bromo-7-chloroquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 71721309HCID 71721309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a flask containing a stir bar was added 3-bromo-7-chloroquinoline (1.0 g, 4.1 mmol), CuCN (0.55 g, 6.2 mmol) followed by addition of DMF (25 mL). The resulting mixture was then heated to 150° C. overnight. When the reaction was complete as evidenced by LC analyisis, the reaction flask was taken out of the oil bath and cooled to RT. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered. The filtrated was washed with aq. NH4Cl, dried over sodium sulfate, and purified by flash chromatography. LC-MS (IE, m/z): 189 [M+1]+.

Workup

  1. additionTo a flask containing a stir bar
  2. temperaturecooled to RT
  3. filtrationwhich was filtered
  4. washThe filtrated was washed with aq. NH4Cl
  5. dry with materialdried over sodium sulfate
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-acec850ef1c747dda77b6efac48a9afd
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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