3-Bromo-4-fluorobenzaldehyde → HCID 86683819, compound

HRID 1620337Notes

Reaction equation

HRID 1620337 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].[CH3:11][O:12][C:13]1[C:18](B(O)O)=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.O.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>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:18]1[C:13]([O:12][CH3:11])=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 86683819HCID 86683819, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-4-fluorobenzaldehyde (1.0 g, 4.9 mmol), (2-methoxypyridin-3-yl)boronic acid (1.2 g, 7 mmol) and sodium hydrogen carbonate (1.5 g, 15 mmol) was stirred in dioxane (20 mL) and water (8 mL). The mixture was degassed for 10 minutes, then tetrakis(triphenylphosphine)palladium (0) (0.130 g, 0.1 mol) was added. The reaction mixture was stirred at 100° C. for 1 hour then cooled and concentrated in vacuo. The resulting residue was partitioned between EtOAc (60 mL) and water (15 mL), dried over sodium sulfate and concentrated in vacuo to afford the crude product, which was purified by silica gel chromatography eluting with 20% EtOAc in heptane to afford the title compound as a white solid (0.85 g).

Workup

  1. customThe mixture was degassed for 10 minutes
  2. temperaturethen cooled
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was partitioned between EtOAc (60 mL) and water (15 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product, which
  8. customwas purified by silica gel chromatography
  9. washeluting with 20% EtOAc in heptane

Sources & evidence

ORD record
ord-113c2698ac164fcbac358b00e0f84170
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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