Water → HCID 21071594, compound

HRID 1014172Notes

Reaction equation

HRID 1014172 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](OC)[CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.[C:22]([O-])([O-])=O.[Na+].[Na+].O>C(OCC)(=O)C>[CH3:22][C:4]1[CH:3]=[C:2]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 811105-Chloro-2-nitroanisoleHCID 27343783-Pyridinylboronic acid

Product 1

HCID 21071594HCID 21071594, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
82 °C

Procedure

Nitrogen was bubbled through dioxane for 15 minutes (100 mL) prior to the addition of 4-chloro-2-(methyloxy)-1-nitrobenzene (5.0 g, 29.1 mmol, Aldrich). To the solution were added 3-pyridinylboronic acid (4.3 g, 34.9 mmol, Frontier Science), dichloro(triphenylphosphine)palladium (1.0 g, 1.46 mmol, Aldrich) and degassed aqueous Na2CO3 (30 mL, 3 N, 87.3 mmol). The reaction mixture was heated at 82° C. for 4 h. Additional water (100 mL) was added to the reaction when it was cooled down to rt, and ethyl acetate was used to extract the crude product. The combined organic phases were dried (Na2CO3), concentrated, and purified by silica column chromatography (10-60% Ethyl acetate/hexane) to afford 3-(3-methyl-4-nitrophenyl)pyridine (5.3 g, 85% yield.) 1H NMR (400 MHz, DMSO-d6) δ ppm 2.58 (s, 3 H), 7.52 (ddd, J=8.0, 4.8, 0.9 Hz, 1 H), 7.80 (dd, J=8.5, 2.1 Hz, 1 H), 7.90 (d, J=1.1 Hz, 1 H), 8.08 (d, J=8.4 Hz, 1 H), 8.16 (ddd, J=8.0, 2.5, 1.6 Hz, 1 H), 8.62 (dd, J=4.8, 1.5 Hz, 1 H), 8.95-8.97 (m, 1 H).

Workup

  1. customNitrogen was bubbled through dioxane for 15 minutes (100 mL)
  2. temperaturewas cooled down to rt
  3. extractionto extract the crude product
  4. dry with materialThe combined organic phases were dried (Na2CO3)
  5. concentrationconcentrated
  6. custompurified by silica column chromatography (10-60% Ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eb4ce78777c64aeebe2c23d78dbf6104
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…