Dimethylformamide → HCID 68822450, compound

HRID 2101765Notes

Reaction equation

HRID 2101765 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6](Br)[CH:5]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1B(O)O.[C:25](=[O:28])([O-])[O-:26].[K+].[K+].[CH3:31]N(C=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.C1(C)C=CC=CC=1>[CH3:31][O:26][C:25]([C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[C:9]([C:15]2[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=2[F:13])[CH:4]=1)=[O:28]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 22352523Methyl 3-bromo-4-chlorobenzoate

Product 1

HCID 68822450HCID 68822450, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a round bottom flask containing 13.1 (1.75 g, 7.01 mmol), 2-fluoro-5-methoxyphenylboronic acid (2.0 g, 11.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.81 g, 0.70 mmol), and potassium carbonate (2.91 g, 21.0 mmol) was added a premixed 3:1 solution of toluene (18 mL) and DMF (6 mL, 7.01 mmol). The mixture was heated at 100° C. and monitored with TLC. After 17 hours, the reaction was cooled to room temperature then partitioned between EtOAc and water. The aqueous layer was further extracted with EtOAc (2×20 mL). The organic layers were combined, washed with brine, and dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtering, and the organic phase was concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes) to yield a colorless oil 13.2 (1.01 g, 49% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 8.04 (1H, m), 8.02 (1H, m) 7.57 (1H, d, J=8.2 Hz), 7.09 (1H, t, J=9.0 Hz), 6.93 (1H, dt, J=9.0, 3.5 Hz), 6.82 (1H, dd, J=5.1, 3.1 Hz), 3.93 (3H, s), 3.83 (3H, s).

Workup

  1. additionwas added
  2. temperaturethe reaction was cooled to room temperature
  3. customthen partitioned between EtOAc and water
  4. extractionThe aqueous layer was further extracted with EtOAc (2×20 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe magnesium sulfate was removed
  8. filtrationby filtering
  9. concentrationthe organic phase was concentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b0b54161f63a4f20b3580be1d1f0e0ab
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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