Dimethylformamide → HCID 86635915, compound

HRID 561802Notes

Reaction equation

HRID 561802 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:12][C:13]#[N:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.CN([CH:18]=[O:19])C.C([O-])=O.[Na+]>O>[CH:18]([C:2]1[CH:3]=[C:4]([CH2:12][C:13]#[N:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)=[O:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2723810Sodium FormateHCID 21865581HCID 21865581, compound

Product 1

HCID 86635915HCID 86635915, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (8-bromoquinolin-6-yl)acetonitrile (1 eq.) in anhydrous, deoxygenated DMF (0.08 M) was added freshly-dried sodium formate (1.5 eq.) and Pd(PPh3)Cl2 (2% loading). Through the resulting yellow suspension, was bubbled CO and then reaction was heated to 80° C. for 16 h. The now black reaction suspension was cooled to RT, diluted with water, and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound.

Workup

  1. customThrough the resulting yellow suspension, was bubbled CO
  2. customreaction
  3. temperatureThe now black reaction suspension was cooled to RT
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5b38a01cee904a98a5fff4480807eb35
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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