Triphenylphosphine → HCID 136166843, compound

HRID 1617454Notes

Reaction equation

HRID 1617454 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.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F-].[K+].[NH4+].[Cl-]>CC(N(C)C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]1([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:29]3[CH:30]=[N:25][CH:26]=[N:27][CH:28]=3)=[CH:3][CH:4]=2)[CH2:9]/[C:10](/[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:11]\[OH:12])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 522689Potassium FluorideHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 136167080HCID 136167080, compound

Product 1

HCID 136166843HCID 136166843, compoundYield 451%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21534740N,N-Dimethylacetamide--water (1/1)Solvent

Procedure

To a stirred solution of (E)-3-(4-bromo-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (example 5, 10 mg) and pyrimidine-5-boronic acid (49 mg) in a mixture of DMA/H2O (2.1 mL, 20:1) tetrakis(triphenylphosphine)palladium (0) (36 mg), triphenylphosphine (17 mg) and potassium fluoride (31 mg) were added. The mixture was irradiated in the microwave at 140° C. for 15 min. A saturated aqueous solution of NH4Cl 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 an ISOLUTE Flash NH2 cartridge (EtOAc) to yield the title compound (45 mg, 45%) as a white foam, MS (ESI+): m/z=381.1 ([M+H]+).

Workup

  1. additionwere added
  2. customThe mixture was irradiated in the microwave at 140° C. for 15 min
  3. customthe phases were separated
  4. extractionthe inorganic one was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on an ISOLUTE Flash NH2 cartridge (EtOAc)

Sources & evidence

ORD record
ord-8723b02b9efa436390a89b4f5debc9fb
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

Loading…