Potassium Carbonate → 2-Nitro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile

HRID 872484Notes

Reaction equation

HRID 872484 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[N:19]1[C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][CH:21]=[N:20]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-3](Cl)(Cl)C1C(Cl)=CC=CN=1)(C)C>[N+:10]([C:5]1[CH:4]=[CH:3][C:2]([C:23]2[N:19]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][O:13]3)[N:20]=[CH:21][CH:22]=2)=[CH:9][C:6]=1[C:7]#[N:8])([O-:12])=[O:11]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1005065-Chloro-2-nitrobenzonitrileHCID 115872081-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 671725352-Nitro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile

Reagents, catalysts & solvents 3

HCID 178439029HCID 178439029, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-nitrobenzonitrile (1.5 g), 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.74 g), PEPPSI ((1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) (3-chloropyridyl)palladium(ii) dichloride) (0.11 g), K2CO3 (2.27 g) in DMF (30 ml) and water (3 ml) was stirred under argon at 90° C. for 2.5 h. After pouring the mixture to water, it was extracted with EtOAc. Combined organic phases were washed with 5% NaHCO3, water and brine, dried with Na2SO4 and evaporated. The residue was triturated with ethanol. The precipitate was filtered and washed with water. Yield 1.96 g. 1H-NMR (400 MHz; d6-DMSO): δ 1.50-1.65 (m, 3H), 1.83-1.87 (m, 1H), 1.95-1.99 (m, 1H), 2.33-2.42 (m, 1H), 3.60-3.67 (m, 1H), 3.95-4.00 (m, 1H), 5.34 (d, 1H), 6.82 (d, 1H), 7.68 (d, 1H), 8.11 (dd, 1H), 8.32 (d, 1H), 8.54 (d, 1H).

Workup

  1. extractionwas extracted with EtOAc
  2. washCombined organic phases were washed with 5% NaHCO3, water and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe residue was triturated with ethanol
  6. filtrationThe precipitate was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-cb9b407d3f254210810a7b50c1174988
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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