Potassium Carbonate → HCID 22179824, compound

HRID 270029Notes

Reaction equation

HRID 270029 reaction equation
FC(F)(F)C(O[C:6]1[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][CH:7]=1)=O.C([Sn](CCCC)(CCCC)[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)CCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[CH3:13][C:9]1([CH3:12])[CH2:10][CH2:11][C:6]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:7][CH2:8]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 22179857HCID 22179857, compound

Product 1

HCID 22179824HCID 22179824, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 12A (0.775 g. 3.0 mmol) and 4-tributylstannylpyridine (1.22 g, 3.3 mmol) in 1-methyl-2-pyrrolidinone (5 mL) was treated with Pd2(dba)3 (55 mg, 0.06 mmol), CuI (65 mg, 0.35 mmol), Ph3P (125 mg, 0.475 mmol) and K2CO3 (550 mg, 3.9 mmol), purged with argon, and stirred for 25 hours at 90° C. The reaction mixture was diluted with ethyl acetate (50 mL) and saturated aqueous potassium fluoride (10 mL), stirred 2 hours at room temperature, and filtered through a pad of diatomaceous earth (Celite®). The filtrate layers were separated and the organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:1 ethyl acetate and hexanes to provide 200 mg (36%) of the desired product. MS (ESI) m/e 188.1 (M+H)+.

Workup

  1. custompurged with argon
  2. additionThe reaction mixture was diluted with ethyl acetate (50 mL) and saturated aqueous potassium fluoride (10 mL)
  3. stirringstirred 2 hours at room temperature
  4. filtrationfiltered through a pad of diatomaceous earth (Celite®)
  5. customThe filtrate layers were separated
  6. washthe organic phase was washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by flash column chromatography on silica gel with 4:1 ethyl acetate and hexanes

Sources & evidence

ORD record
ord-687d49d5df754ab7915427c304fcc454
Source dataset
uspto-grants-2008_11
Patent number
US07449485B2

Reaction notes

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