Sodium Carbonate → HCID 58514136, compound

HRID 1910734Notes

Reaction equation

HRID 1910734 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16](Br)[CH:15]=1)=[O:13].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:7]=[C:6]([C:16]2[CH:15]=[C:14]([C:12](=[O:13])[CH3:11])[CH:19]=[CH:18][CH:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 165023'-BromoacetophenoneHCID 51515952-Chloropyridine-4-boronic acid

Product 1

HCID 58514136HCID 58514136, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloropyridine-4-boronic acid (11.0 g, 69.9 mmol), 3-Bromoacetophenone (11.2 mL, 83.9 mmol, 1.2 eq.), Na2CO3 (35 mL, 244.65 mmol, 3.5 eq.) and dppfPdCl2 (572 mg, 0.07 mmol, 0.01 eq.) were mixed in THF (200 mL). The mixture was heated to reflux and continued at this temperature for 6 hours. It was then cooled and concentrated in vacuo. The residue was partitioned between DCM and water (100 mL/40 mL). The layers were separated and the aqueous layer was washed further with DCM (2×40 mL). The combined organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated, and the residue was chromatographed using 1/1 hexane/EtOAc to give 1-[3-(2-Chloro-pyridin-4-yl)-phenyl]-ethanone as a white solid (9.5 g, 58%). MS: m/z 232.1 [MH+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureIt was then cooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between DCM and water (100 mL/40 mL)
  6. customThe layers were separated
  7. washthe aqueous layer was washed further with DCM (2×40 mL)
  8. dry with materialThe combined organic layer was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customthe residue was chromatographed

Sources & evidence

ORD record
ord-ba11818520fa4fa1a3d0bfc7ae407a46
Source dataset
uspto-grants-2013_12
Patent number
US08604031B2

Reaction notes

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