Dimethyl Sulfoxide → HCID 90118372, compound

HRID 523157Notes

Reaction equation

HRID 523157 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=2)[N:3]=1.[F-:23].[Cs+].CS(C)=O>CCOC(C)=O>[F:23][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=2)[N:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 25953Cesium fluorideHCID 90118308HCID 90118308, compound

Product 1

HCID 90118372HCID 90118372, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 2 dram vial equipped with a stir bar and charged with 2-chloro-6-(4-isopropoxyphenyl)-4-(1H-pyrazol-1-yl)pyridine (41 mg, 0.13 mmol) was added CsF (199 mg, 1.31 mmol), then DMSO (0.7 mL). The vial was placed in a 140° C. heating block with vigorous stirring for 18 hours. The reaction mixture was transfered to a separatory funnel and was diluted with EtOAc (50 mL). The organic solution was washed twice with brine:water (25 mL:25 mL); dried over MgSO4; filtered; then concentrated in vacuo to afford 2-fluoro-6-(4-isopropoxyphenyl)-4-(1H-pyrazol-1-yl)pyridine as a yellow solid (25 mg, 63%). 1H-NMR (500 MHz, CDCl3) δ 8.07 (dd, J=2.6, 0.4 Hz, 1H), 8.03-7.99 (m, 2H), 7.95 (t, J=1.4 Hz, 1H), 7.81 (d, J=1.4 Hz, 1H), 7.09 (t, J=1.6 Hz, 1H), 7.01-6.97 (m, 2H), 6.57 (dd, J=2.7, 1.7 Hz, 1H), 4.65 (spt, J=6.1 Hz, 1H), 1.39 (d, J=6.1 Hz, 6H); MS: MS m/z 298.2 (M++1).

Workup

  1. customTo a 2 dram vial equipped with a stir bar
  2. customwas placed in a 140° C.
  3. temperatureheating block
  4. customThe reaction mixture was transfered to a separatory funnel
  5. washThe organic solution was washed twice with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-b9dc6542543e4ddc81a45e979131c5e4
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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