Sodium Carbonate → HCID 66652889, compound

HRID 2283633Notes

Reaction equation

HRID 2283633 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1B(O)O.[NH2:16][C:17]1[CH:22]=[C:21](Br)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:21]1[CH:20]=[CH:19][N:18]=[C:17]([NH2:16])[CH:22]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 6932822-Amino-4-bromopyridineHCID 27826762-Methoxy-5-(trifluoromethyl)phenylboronic acid

Product 1

HCID 66652889HCID 66652889, compoundYield 120%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

Argon was bubbled through a suspension of 2-methoxy-5-trifluoromethylphenylboronic acid (2.3 g, 10 mmol), 2-amino-4-bromopyridine (2.0 g, 12 mmol), and sodium carbonate (4.4 g, 42 mmol) in 1,4-dioxane (30 mL) and water (9 mL) for 15 minutes, then tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.0 mmol) was added. The resulting mixture was heated at 85° C. for 18 hours. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate and water. The phases were separated and the aqueous phase extracted with ethyl acetate then choloroform. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (0% to 10% methanol in chloroform gradient elution) to afford the title compound as yellow oil (3.22 g).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (0% to 10% methanol in chloroform gradient elution)

Sources & evidence

ORD record
ord-c733f64428734b1abde9cab7d62f083c
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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