Sodium Carbonate → HCID 118497072, compound

HRID 522143Notes

Reaction equation

HRID 522143 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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].O>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27628032-Bromo-3-fluoropyridineHCID 46739435Methyl 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 118497072HCID 118497072, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.67 g, 5.30 mmol) in THF (10 mL) was added 2-bromo-3-fluoropyridine (933 mg, 5.30 mmol), tri(o-tolyl)phosphine (67 mg, 0.22 mmol), Na2CO3 (2.25 g, 21.2 mmol) and water (1.6 mL) and the reaction was purged with nitrogen for 15 minutes. Bis(dibenzylidene acetone)palladium (63 mg, 0.11 mmol) was added with further purging with nitrogen for 10 minutes before heating at 80° C. for 1 hour. The reaction was cooled to room temperature and filtered through a pad of arbocel, washing through with EtOAc (50 mL). The filtrate was washed with water (50 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 10-20% EtOAc in heptanes to afford the title compound (240 mg, 21%).

Workup

  1. customthe reaction was purged with nitrogen for 15 minutes
  2. customwith further purging with nitrogen for 10 minutes
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered through a pad of arbocel
  5. washwashing through with EtOAc (50 mL)
  6. washThe filtrate was washed with water (50 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. washeluting with 10-20% EtOAc in heptanes

Sources & evidence

ORD record
ord-f8344bf7f30c485381b699bf797e9c93
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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