Potassium Carbonate → HCID 57418745, compound

HRID 1897433Notes

Reaction equation

HRID 1897433 reaction equation
C([Si]([S:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[N:16]=[CH:15]2)(C(C)C)C(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+].F[C:31]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:32]=1[C:33]#[N:34]>CN(C=O)C>[CH3:21][N:17]1[C:18]2[C:14](=[CH:13][C:12]([S:11][C:31]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:32]=3[C:33]#[N:34])=[CH:20][CH:19]=2)[CH:15]=[N:16]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 1235582,5-DifluorobenzonitrileHCID 57418744HCID 57418744, compound

Product 1

HCID 57418745HCID 57418745, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Compound (3r) (0.65 g, 2 mmol), potassium carbonate (0.34 g, 2.4 mmol), CsF (0.46 g, 3 mmol), 2,5-difluorobenzonitrile (0.56 g, 4.1 mmol) and DMF (5 mL) were placed in a 60 mL reaction vial and the vial was sealed. The mixture was heated to 100° C. for 16 hours. Excess DMF was removed under reduced pressure. This material was taken up in DCM (50 mL) and washed with water (20 mL). The aqueous layer was extracted with DCM (3×). The combined organic layers were washed with brine (2×) and dried over MgSO4, filtered through a plug of celite/silica gel and concentrated under reduced pressure. The residue was purified by silica gel chromatography with hexane/EtOAc (20%) to give the final product as a viscous liquid (4r) (0.43 g, 75% isolated yield). 1H NMR (400 MHz, CDCl3) δ 7.99 (s, 1H), 7.97 (s, 1H), 7.46 (dd, J=16.8, 8.8 Hz, 2H), 7.35-7.32 (m, 1H), 7.14-7.07 (m, 1H), 7.05-7.01 (m, 1H), 4.1 (s, 3H); MS (ESI) m/z 284.2 (M+H)+.

Workup

  1. customthe vial was sealed
  2. customExcess DMF was removed under reduced pressure
  3. washwashed with water (20 mL)
  4. extractionThe aqueous layer was extracted with DCM (3×)
  5. washThe combined organic layers were washed with brine (2×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through a plug of celite/silica gel
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography with hexane/EtOAc (20%)

Sources & evidence

ORD record
ord-d5528bf55e3845ac8ca019a002b30408
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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