Dimethylformamide → Quinoline-7-carbonitrile

HRID 656888Notes

Reaction equation

HRID 656888 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1)(=O)=O.[CH3:19][N:20](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:14]1[C:15]2[C:10](=[CH:9][CH:8]=[C:7]([C:19]#[N:20])[CH:16]=2)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 59296115Quinolin-7-yl trifluoromethanesulfonate

Product 1

HCID 22344048Quinoline-7-carbonitrileYield 97%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A solution of 7-quinolinyl trifluoromethanesulfonate (1.88 g, 6.8 mmol) in DMF (40 ml) was degassed for 10 minutes with Argon. Zinc(II) cyanide (0.48 g, 4.08 mmol), tris(dibenzylideneacetone)dipalladium(0) (155 mg, 2.5% mmol) and 1,1′-bis(diphenylphospino)ferrocene (188 mg, 5% mmol) was then added and the mixture was heated at 100° C. under argon for 1.5 h. The solvent was evaporated and residue dissolved in DCM and organic phase washed with a saturated solution of sodium bicarbonate. The aqueous phase was extracted with DCM (3×80 ml). The combined organic phases were dried, evaporated and the residue was chromatographed on silica gel, eluting with 0-10% methanol-DCM to afford the desired compound (1.01 g, 97%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionresidue dissolved in DCM
  3. washorganic phase washed with a saturated solution of sodium bicarbonate
  4. extractionThe aqueous phase was extracted with DCM (3×80 ml)
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customthe residue was chromatographed on silica gel
  8. washeluting with 0-10% methanol-DCM

Sources & evidence

ORD record
ord-d792e94b31e84391bfbf3961eecc53b1
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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