Potassium Carbonate → benzyl 4-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 2196536Notes

Reaction equation

HRID 2196536 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:12]=2)[N:9]=[C:8]([C:26]([F:29])([F:28])[F:27])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:49])[CH2:44][CH:43]=1)(=O)=O>CN(C=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([C:42]3[CH2:47][CH2:46][N:45]([C:48]([O:50][CH2:51][C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)=[O:49])[CH2:44][CH:43]=3)[CH:14]=[CH:15][CH:16]=2)[N:9]=[C:8]([C:26]([F:29])([F:28])[F:27])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11303044benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylateHCID 598433125-(furan-2-yl)-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 59843270benzyl 4-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylateYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 63 (533 mg, 1.319 mmol) in DMF (6.6 mL) were added potassium carbonate (419 mg, 3.03 mmol) and benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1 (2H)-carboxylate (578 mg, 1.582 mmol) followed by 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (58 mg, 0.079 mmol). The resulting suspension was allowed to stir at 75° C. for 4 h. The mixture then was filtered through celite and washed with EtOAc. The organic phase was washed with brine and dried over Na2SO4. The solution was then evaporated to dryness. The residue was purified via silica gel flash chromatography (5% to 40% EtOAc/hexanes). The title product 64 (430 mg, 66% yield) was isolated as a colorless oil. LRMS (ESI): calc. 493.5; found 494.5 (MH)+.

Workup

  1. filtrationThe mixture then was filtered through celite
  2. washwashed with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solution was then evaporated to dryness
  6. customThe residue was purified via silica gel flash chromatography (5% to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dfa2442293dc4e2f9630f3b96f06f6cf
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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