Sodium Bicarbonate → HCID 136166894, compound

HRID 1617449Notes

Reaction equation

HRID 1617449 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]/[C:10](/[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:11]\[OH:12])=[CH:4][CH:3]=1.[CH:25]1([B-](F)(F)F)[CH2:27][CH2:26]1.[K+].O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:25]1([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9]/[C:10](/[C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:11]\[OH:12])=[CH:4][CH:3]=2)[CH2:27][CH2:26]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 23697338Potassium cyclopropyltrifluoroborateHCID 136167080HCID 136167080, compound

Product 1

HCID 136166894HCID 136166894, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (E)-3-(4-bromo-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (example 5, 100 mg) in toluene (0.9 mL) and water (0.1 mL) was added potassium cyclopropyltrifluoroborate (47 mg), tri-potassium phosphate monohydrate (199 mg) and tetrakis(triphenylphosphine) palladium (0) (6 mg). The mixture was heated to 100° C. overnight. After cooling to rt a saturated aqueous solution of NaHCO3 was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield (E)-3-(4-cyclopropyl-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (43 mg, 49%) as a white foam, MS (ESI+): m/z=343.3 ([M+H]+).

Workup

  1. additionwas added
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1)

Sources & evidence

ORD record
ord-c4f9373b47304128971d69706e5982b2
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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