Potassium Carbonate → HCID 69043784, compound

HRID 877959Notes

Reaction equation

HRID 877959 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34].[C:36]1([CH3:45])[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1B(O)O>O1CCOCC1>[N+:33]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:27]=1[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[CH3:45])([O-:35])=[O:34]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27332672-Methylphenyl boronic acidHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 69043784HCID 69043784, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Triphenylphosphine (2.10 g, 1.89 mmol) and potassium carbonate (7.80 g, 56.7 mmol) were added to a slurry of 4-chloro-3-nitropyridine (3.00 g, 18.9 mmol, CAS RN 13091-23-1) and 2-tolylboronic acid (2.83 g, 20.8 mmol, CAS RN 16419-60-6) in dioxane stirring under an argon atmosphere. The reaction mixture was heated to 120° C. for 16 hours and then cooled to room temperature. The solids were removed by filtration through celite and all volatiles were removed in vacuo resulting in a dark colored heavy oil. The product was isolated as a heavy oil by flash chromatography on silica gel (25-33% EtOAc in n-hexane) (1.75 g, 43%).

Workup

  1. temperaturecooled to room temperature
  2. customThe solids were removed by filtration through celite
  3. customall volatiles were removed in vacuo
  4. customresulting in a dark colored heavy oil
  5. customThe product was isolated as a heavy oil by flash chromatography on silica gel (25-33% EtOAc in n-hexane) (1.75 g, 43%)

Sources & evidence

ORD record
ord-825e8b6752f748d291579c59f8431e4e
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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